Compound characterization data — Schriefer Treiber et al., 2026

Manuel G. Schriefer Treiber, Bryce D. Delgado, Joy Becher, Przemysław Dutka, Mattis Hilleke, Irene Pachon Angona, Josefa dela Cruz-Chuh, Shu Ti, Laëtitia Comps-Agrar, Petra Schneider, Jan A. Hiss, Achi Haider, Kenneth Atz, Matthieu Masureel, Uwe Grether, Gisbert Schneider. “Learning from nature: De novo generative design of natural-product-inspired opioid agonists.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007728/v1

Tert-Butyl 4-benzylpiperazine-1-carboxylate
Identifier	SI-2
¹H NMR (500 MHz, CDCl₃)	δ 7.36–7.29 (m, 4H), 7.28–7.24 (m, 1H), 3.51 (s, 2H), 3.48–3.38 (m, 4H), 2.45–2.33 (m, 4H), 1.45 (s, 9H)

1-benzylpiperazine / BZP
Identifier	SI-3
¹H NMR (400 MHz, CDCl₃)	δ 7.35–7.27 (m, 4H), 7.27–7.21 (m, 1H), 3.49 (s, 2H), 2.90 (t, J = 4.9 Hz, 4H), 2.42 (br. s, 4H), 1.94 (s, 1H)

N-(3-hydroxypropyl)-N-methylbenzamide
Identifier	SI-5
¹H NMR (400 MHz, CDCl₃)	δ 7.50–7.30 (m, 5H), 3.94–2.84 (m, 8H), 1.91–1.69 (m, 2H)

N-(3-bromopropyl)-N-methylbenzamide
Identifier	SI-6
¹H NMR (400 MHz, CDCl₃)	δ 7.46–7.33 (m, 5H), 3.77–3.54 (m, 1H), 3.53–2.90 (m, 6H), 2.40–1.95 (m, 2H)

N-(3-(4-benzylpiperazin-1-yl)propyl)-N-methylbenzamide
Identifier	3
¹H NMR (400 MHz, CDCl₃)	δ 8.03 (d, J = 7.5 Hz, 0.39H), 7.55 (t, J = 7.5 Hz, 0.39H), 7.44 (t, J = 7.5 Hz, 0.39H), 7.41–7.34 (m, 4.76H), 7.34–7.27 (m, 3H), 7.27–7.20 (m, 1H), 4.47–4.18 (m, 0.42H), 3.66–3.40 (m, 2.65H), 3.36–3.30 (m, 1H), 3.13–2.88 (m, 3H), 2.83–1.50 (m, 12H)
¹³C NMR (101 MHz, CDCl₃)	δ 171.8, 138.0, 136.8, 133.0, 129.6, 129.4, 128.5, 128.3, 127.2, 127.0, 126.7, 63.3, 63.1, 55.8, 55.2, 53.2, 53.1, 52.9, 49.7, 45.9, 37.8, 33.0, 26.7, 25.7, 24.5 (mixture of different conformers, major signals given, some signals only observed by HMBC)
HRMS (ESI-TOF) [M+H]⁺	m/z: 352.2383 calculated for C₂₂H₃₀N₃O, found: 352.2379

3·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 13.00-11.00 (m, 1H), 7.75-7.18 (m, 10H), 4.76-4.00 (m, 2H), 3.93-3.03 (m, 18H, including H₂O), 3.03-2.76 (m, 4H), 2.20-1.80 (m, 2H)
¹H NMR (400 MHz, MeOD-d₄)	δ 7.66-7.35 (m, 10H), 4.54-4.28 (m, 2H), 4.16-3.32 (m, 12H), 3.16-3.00 (m, 3H), 2.30-1.94 (m, 2H)

1-(2,3-dimethylphenyl)piperazine
Identifier	SI-9
¹H NMR (400 MHz, CDCl₃)	δ 7.08 (t, J = 7.7 Hz, 1H), 6.95–6.88 (m, 2H), 3.08–3.01 (m, 4H), 2.91–2.80 (m, 4H), 2.27 (s, 3H), 2.23 (s, 3H), 2.04 (br. s, 1H)

Tert-Butyl (3-bromopropyl)carbamate
Identifier	SI-11
¹H NMR (400 MHz, CDCl₃)	δ 4.67 (br. s, 1H), 3.43 (t, J = 6.5 Hz, 2H), 3.33–3.19 (m, 2H), 2.04 (quin, J = 6.5 Hz, 2H), 1.43 (s, 9H)

Tert-Butyl (3-(4-(2,3-dimethylphenyl)piperazin-1-yl)propyl)carbamate
Identifier	SI-12
¹H NMR (400 MHz, CDCl₃)	δ 7.07 (t, J = 7.7 Hz, 1H), 6.95–6.87 (m, 2H), 5.52 (br. s, 0.86H), 5.03 (br. s, 0.13H), 3.29–3.14 (m, 2H), 2.98–2.86 (m, 4H), 2.63 (br. s, 4H), 2.55–2.45 (m, 2H), 2.27 (s, 3H), 2.22 (s, 3H), 1.72 (quin, J = 6.4 Hz, 2H), 1.45 (s, 9H)

N-(3-(4-(2,3-dimethylphenyl)piperazin-1-yl)propyl)benzamide
Identifier	4
¹H NMR (400 MHz, CDCl₃)	δ 8.40 (br. s, 1H), 7.91–7.84 (m, 2H), 7.51–7.46 (m, 1H), 7.46–7.39 (m, 2H), 7.11 (t, J = 7.7 Hz, 1H), 6.93 (d, J = 7.4 Hz, 1H), 6.87 (d, J = 7.9 Hz, 1H), 3.67–3.56 (m, 2H), 3.06–2.88 (m, 4H), 2.88–2.35 (m, 6H), 2.27 (s, 3H), 2.21 (s, 3H), 1.85 (quin, J = 5.9 Hz, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 167.4, 151.4, 138.2, 135.0, 131.5, 131.3, 128.5, 127.2, 126.0, 125.3, 116.6, 58.6, 54.0, 52.1, 41.0, 24.4, 20.7, 14.0
HRMS (ESI-TOF) [M+H]⁺	m/z: 352.2383 calculated for C₂₂H₃₀N₃O, found: 352.2382

4·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 10.88 (s, 1H), 8.81–8.67 (m, 1H), 7.94–7.86 (m, 2H), 7.57–7.51 (m, 2H), 7.51–7.43 (m, 2H), 7.07 (t, J = 7.6 Hz, 1H), 6.93 (d, J = 7.5 Hz, 1H), 6.90 (d, J = 8.0 Hz, 1H), 3.59–3.48 (m, 2H), 3.42–3.32 (m, 2H), 3.28–3.04 (m, 8H), 2.21 (s, 3H), 2.16 (s, 3H), 2.09–1.96 (m, 2H)

1-(4-(3-bromopropoxy)phenyl)ethan-1-one
Identifier	SI-15
¹H NMR (400 MHz, CDCl₃)	δ 7.96–7.91 (m, 2H), 6.96–6.91 (m, 2H), 4.17 (t, J = 5.8 Hz, 2H), 3.60 (t, J = 6.4 Hz, 2H), 2.55 (s, 3H), 2.34 (quin, J = 6.1 Hz, 2H)

1-(4-fluorophenyl)piperazine
Identifier	SI-17
¹H NMR (400 MHz, CDCl₃)	δ 7.00–6.91 (m, 2H), 6.91–6.84 (m, 2H), 3.09–3.01 (m, 8H), 1.92 (br. s, 1H)

1-(4-(3-(4-(4-fluorophenyl)piperazin-1-yl)propoxy)phenyl)ethan-1-one
Identifier	5
¹H NMR (400 MHz, CDCl₃)	δ 7.95–7.90 (m, 2H), 7.00–6.91 (m, 4H), 6.91–6.84 (m, 2H), 4.11 (t, J = 6.3 Hz, 2H), 3.16–3.10 (m, 4H), 2.67–2.62 (m, 4H), 2.59 (t, J = 7.2 Hz, 2H), 2.55 (s, 3H), 2.03 (quin, J = 7.2 Hz, 2H)
¹⁹F NMR (377 MHz, CDCl₃)	δ –124.6
¹³C NMR (101 MHz, CDCl₃)	δ 196.8, 163.0, 157.1 (d, J = 238.5 Hz), 148.0 (d, J = 2.2 Hz), 130.7, 130.4, 117.9 (d, J = 7.6 Hz), 115.6 (d, J = 22.1 Hz), 114.2, 66.5, 55.0, 53.3, 50.2, 26.7, 26.4
HRMS (ESI-TOF) [M+H]⁺	m/z: 357.1973 calculated for C₂₁H₂₆FN₂O₂, found: 357.1969

5·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 11.01 (br. s, 1H), 7.97–7.91 (m, 2H), 7.15–6.99 (m, 6H), 4.19 (t, J = 6.0 Hz, 2H), 3.80–3.67 (m, 2H), 3.67–3.54 (m, 2H), 3.36–3.26 (m, 2H), 3.23–3.08 (m, 4H), 2.52 (s, 3H), 2.32–2.22 (m, 2H)

1-(2-methoxyphenyl)-4-(3-phenoxypropyl)piperazine
Identifier	6
¹H NMR (400 MHz, CDCl₃)	δ 7.32–7.26 (m, 2H), 7.04–6.89 (m, 6H), 6.87 (dd, J = 7.9, 1.3 Hz, 1H), 4.05 (t, J = 6.4 Hz, 2H), 3.87 (s, 3H), 3.12 (br. s, 4H), 2.70 (br. s, 4H), 2.65–2.57 (m, 2H), 2.03 (quin, J = 6.4 Hz, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 159.1, 152.4, 141.5, 129.5, 123.0, 121.1, 120.7, 118.3, 114.6, 111.3, 66.3, 55.5, 55.4, 53.6, 50.8, 26.9
HRMS (ESI-TOF) [M+H]⁺	m/z: 327.2067 calculated for C₂₀H₂₇N₂O₂, found: 327.2064

6·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 11.48 (br. s, 1H), 7.34–7.25 (m, 2H), 7.08–6.87 (m, 7H), 4.07 (t, J = 6.1 Hz, 2H), 3.80 (s, 3H), 3.64–3.43 (m, 4H), 3.34–3.13 (m, 6H), 2.32–2.19 (m, 2H)

1-(3-methoxyphenyl)-4-(3-phenoxypropyl)piperazine
Identifier	7
¹H NMR (400 MHz, CDCl₃)	δ 7.31–7.26 (m, 2H), 7.18 (t, J = 8.2 Hz, 1H), 6.97–6.93 (m, 1H), 6.92–6.88 (m, 2H), 6.55 (dd, J = 8.2, 2.1 Hz, 1H), 6.47 (t, J = 2.3 Hz, 1H), 6.44 (dd, J = 8.1, 2.1 Hz, 1H), 4.06 (t, J = 6.2 Hz, 2H), 3.79 (s, 3H), 3.35–3.24 (m, 4H), 2.84–2.64 (m, 6H), 2.10 (quin, J = 7.0 Hz, 2H)
¹³C NMR (126 MHz, CDCl₃)	δ 160.7, 159.1, 152.8, 129.8, 129.5, 120.7, 114.6, 108.9, 104.4, 102.5, 66.1, 55.3, 55.2, 53.3, 49.1, 26.9
HRMS (ESI-TOF) [M+H]⁺	m/z: 327.2067 calculated for C₂₀H₂₇N₂O₂, found: 327.2065

7·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 11.48 (br. s, 1H), 7.34–7.25 (m, 2H), 7.08–6.87 (m, 7H), 4.07 (t, J = 6.1 Hz, 2H), 3.80 (s, 3H), 3.64–3.43 (m, 4H), 3.34–3.13 (m, 6H), 2.32–2.19 (m, 2H)

3-(4-Phenylpiperazin-1-yl)propan-1-ol
Identifier	SI-23
¹H NMR (500 MHz, CDCl₃)	δ 7.30–7.24 (m, 2H), 6.97–6.85 (m, 3H), 3.88-3.81 (t, 2H), 3.37–3.21 (m, 4H), 2.96–2.60 (m, 6H), 1.82 (quin, J = 5.8 Hz, 2H)

N-methyl-2-(3-(4-phenylpiperazin-1-yl)propoxy)benzamide
Identifier	8
¹H NMR (400 MHz, CDCl₃)	δ 8.22 (dd, J = 6.0, 1.8 Hz, 1H), 7.90 (s, 1H), 7.41 (ddd, J = 8.4, 7.4, 1.8 Hz, 1H), 7.30–7.24 (m, 1H), 7.10–7.04 (m, 1H), 7.01–6.96 (m, 1H), 6.96–6.91 (m, 2H), 6.90–6.83 (m, 1H), 4.23 (t, J = 6.4 Hz, 2H), 3.27–3.18 (m, 4H), 3.02 (d, J = 4.8 Hz, 3H), 2.69–2.63 (m, 4H), 2.63–2.56 (t, J = 7.1 Hz, 2H), 2.11 (quin, J = 7.1 Hz, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 166.2, 156.9, 151.3, 132.7, 132.4, 129.3, 121.9, 121.5, 120.0, 116.2, 112.5, 67.4, 55.2, 53.5, 49.2, 26.7
HRMS (ESI-TOF) [M+H]⁺	m/z: 354.2176 calculated for C₂₁H₂₈N₃O₂, found: 354.2174

8·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 11.25 (br. s, 1H), 8.09 (m, 1H), 7.66 (dd, J = 7.6, 1.8 Hz, 1H), 7.49–7.41 (m, 1H), 7.31–7.23 (m, 2H), 7.14 (d, J = 8.3 Hz, 1H), 7.08–6.97 (m, 3H), 6.87 (t, J = 7.3 Hz, 1H), 4.21 (t, J = 5.9 Hz, 2H), 3.81 (d, J = 12.6 Hz, 2H), 3.60 (d, J = 11.3 Hz, 2H), 3.36–3.08 (m, 6H), 2.82 (d, J = 4.7 Hz, 3H), 2.37–2.25 (m, 2H)

Tert-butyl 4-(3-phenylpropyl)piperazine-1-carboxylate
Identifier	SI-27
¹H NMR (400 MHz, CDCl₃)	δ 7.31–7.24 (m, 2H), 7.21–7.14 (m, 3H), 3.43 (t, J = 5.0 Hz, 4H), 2.64 (t, J = 7.6 Hz, 2H), 2.41–2.31 (m, 6H), 1.86–1.77 (m, 2H), 1.46 (s, 9H)

1-(3-phenylpropyl)piperazine
Identifier	SI-28
¹H NMR (400 MHz, CDCl₃)	δ 7.30–7.24 (m, 2H), 7.21–7.14 (m, 3H), 2.89 (t, J = 5.0 Hz, 4H), 2.63 (t, J = 7.7 Hz, 2H), 2.49–2.32 (m, 6H), 1.87–1.76 (m, 2H)

1-Phenyl-2-(4-(3-phenylpropyl)piperazin-1-yl)ethan-1-one
Identifier	9
¹H NMR (400 MHz, CDCl₃)	δ 8.02–7.97 (m, 2H), 7.58–7.53 (m, 1H), 7.48–7.42 (m, 2H), 7.30–7.24 (m, 2H), 7.21–7.15 (m, 3H), 3.81 (s, 2H), 2.83–2.45 (m, 10H), 2.43–2.37 (m, 2H), 1.83 (quin, J = 7.7 Hz, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 196.4, 142.2, 136.2, 133.4, 128.7, 128.5, 128.4, 128.2, 125.9, 64.6, 58.1, 53.6, 53.1, 33.8, 28.6
HRMS (ESI-TOF) [M+H]⁺	m/z: 323.2118 calculated for C₂₁H₂₇N₂O, found: 323.2114

9·2HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 9.07–5.72 (br. s, 1H), 8.01–7.95 (m, 2H), 7.65–7.60 (tt, J = 7.4, 1.3 Hz, 1H), 7.54–7.48 (m, 2H), 3.84 (s, 2H), 2.89–2.51 (m, 6H), 2.51–2.42 (m, 4H), 2.40–2.33 (m, 2H), 1.73 (quin, J = 7.5 Hz, 2H)
¹H NMR (400 MHz, CDCl₃)	δ 12.87 (br. s, 1H), 8.41 (s, 1H), 7.95–7.90 (m, 2H), 7.57 (tt, J = 7.4, 1.3 Hz, 1H), 7.48–7.42 (m, 2H), 7.30–7.24 (m, 2H), 7.22–7.13 (m, 3H), 3.89 (s, 2H), 2.98 (br. s, 4H), 2.84 (br. s, 4H), 2.77–2.71 (m, 2H), 2.65 (t, J = 7.6 Hz, 2H), 2.05–1.94 (m, 2H)

Tert-butyl (1-(cyclohexylmethyl)piperidin-4-yl)carbamate
Identifier	SI-32
¹H NMR (400 MHz, CDCl₃)	δ 4.41 (br. s, 1H), 3.44 (br. s, 1H), 2.89–2.65 (m, 2H), 2.10 (d, J = 7.1 Hz, 2H), 2.00 (t, J = 11.1 Hz, 2H), 1.94–1.82 (m, 2H), 1.80–1.61 (m, 5H), 1.53–1.34 (m, 12H), 1.31–1.06 (m, 3H), 0.94–0.76 (m, 2H)

1-(cyclohexylmethyl)piperidin-4-amine
Identifier	SI-33
¹H NMR (400 MHz, CDCl₃)	δ 2.83–2.72 (m, 2H), 2.66–2.55 (m, 1H), 2.07 (d, J = 7.1 Hz, 2H), 1.90 (t, J = 11.5 Hz, 2H), 1.80–1.60 (m, 7H), 1.52–1.29 (m, 5H), 1.27–1.09 (m, 3H), 0.92–0.76 (m, 2H)

N-(1-(cyclohexylmethyl)piperidin-4-yl)benzo[d]thiazol-2-amine
Identifier	10
¹H NMR (400 MHz, CDCl₃)	δ 7.57 (dd, J = 7.9, 0.9 Hz, 1H), 7.52 (d, J = 8.3 Hz, 1H), 7.31–7.26 (m, 1H), 7.07 (dt, J = 7.8, 1.2 Hz, 1H), 5.35–5.10 (m, 1H), 3.77–3.52 (m, 1H), 2.95–2.74 (m, 2H), 2.24–2.06 (m, 6H), 1.82–1.58 (m, 7H), 1.58–1.41 (m, 1H), 1.34–1.09 (m, 3H), 0.95–0.80 (m, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 166.3, 152.6, 130.6, 126.1, 121.7, 120.9, 119.0, 65.7, 52.7, 52.6, 35.4, 32.4, 32.1, 26.9, 26.3
HRMS (ESI-TOF) m/z [M+H]⁺	calculated for C₁₉H₂₈N₃S: 330.1998, found: 330.1995

10·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 9.83 (s, 1H), 8.81 (br. s, 1H), 7.77–7.69 (m, 1H), 7.45 (d, J = 8.1 Hz, 1H), 7.28 (t, J = 7.6 Hz, 1H), 7.09 (t, J = 7.6 Hz, 1H), 4.26–3.99 (m, 1H), 3.58–3.33 (2×d, J = 12.3 Hz, 2H), 3.30–2.97 (m, 2H), 2.91 (dt, J = 15.5, 5.8 Hz, 2H), 2.28–2.15 (m, 2H), 2.09–1.90 (m, 2H), 1.87–1.73 (m, 3H), 1.73–1.57 (m, 3H), 1.33–1.07 (m, 3H), 1.04–0.89 (m, 2H)
¹H NMR (400 MHz, MeOD-d₄)	δ 7.69 (d, J = 8.0 Hz, 1H), 7.51 (d, J = 8.1 Hz, 1H), 7.41–7.35 (m, 1H), 7.21 (t, J = 7.6 Hz, 1H), 4.27–4.03 (m, 1H), 3.75–3.47 (m, 2H), 3.21–3.10 (m, 2H), 3.09–2.99 (m, 2H), 2.47–2.20 (m, 2H), 2.02–1.67 (m, 8H), 1.45–1.18 (m, 3H), 1.16–1.01 (m, 2H)

N-(1-benzylpiperidin-4-yl)cyclohexanecarboxamide
Identifier	11
¹H NMR (400 MHz, CDCl₃)	δ 7.35–7.23 (m, 5H), 5.27 (d, J = 7.4 Hz, 1H), 3.86–3.75 (m, 1H), 3.52 (s, 2H), 2.83 (d, J = 10.4 Hz, 2H), 2.15 (t, J = 11.1 Hz, 2H), 2.02 (tt, J = 11.7, 3.4 Hz, 1H), 1.94–1.86 (m, 2H), 1.86–1.74 (m, 4H), 1.70–1.62 (m, 1H), 1.54–1.34 (m, 4H), 1.31–1.15 (m, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 175.5, 138.5, 129.2, 128.3, 127.2, 63.2, 52.4, 46.2, 45.8, 32.5, 29.8, 25.9 (2 carbons according to HSQC)
HRMS (ESI-TOF) m/z [M+H]⁺	calculated for C₁₉H₂₉N₂O: 301.2274, found: 301.2276

11·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 11.00 (s, 0.76H), 10.89 (s, 0.24H), 7.93 (d, J = 6.6 Hz, 0.21H), 7.88 (d, J = 7.4 Hz, 0.79H), 7.70–7.56 (m, 2H), 7.51–7.34 (m, 3H), 4.27 (d, J = 5.5 Hz, 0.43H), 4.22 (d, J = 5.3 Hz, 1.55H), 3.95–3.86 (m, 0.22H), 3.77–3.62 (m, 0.79H), 3.30–2.89 (m, 4H), 2.24–1.53 (m, 10H), 1.39–1.04 (m, 5H)

N-(1-benzylpiperidin-4-yl)-2-phenoxyacetamide
Identifier	12
¹H NMR (400 MHz, CDCl₃)	δ 7.36–7.21 (m, 7H), 7.06–7.00 (m, 1H), 6.95–6.88 (m, 2H), 6.44 (d, J = 8.0 Hz, 1H), 4.47 (s, 2H), 3.97–3.85 (m, 1H), 3.49 (s, 2H), 2.87–2.72 (m, 2H), 2.14 (dt, J = 11.6, 2.1 Hz, 2H), 1.96–1.87 (m, 2H), 1.51 (dq, J = 11.3, 3.9 Hz, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 167.6, 157.3, 138.6, 129.9, 129.2, 128.4, 127.2, 122.3, 114.8, 67.5, 63.2, 52.3, 46.3, 32.3
HRMS (ESI-TOF) m/z [M+H]⁺	calculated for C₂₀H₂₅N₂O₂: 325.1911, found: 325.1909

12·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 10.15 (s, 1H), 8.28 (d, J = 7.7 Hz, 0.82H), 8.17 (d, J = 6.7 Hz, 0.18H), 7.59–7.53 (m, 2H), 7.51–7.44 (m, 3H), 7.35–7.25 (m, 2H), 7.01–6.90 (m, 3H), 4.53 (s, 0.36H), 4.46 (s, 1.66H), 4.30 (d, J = 5.6 Hz, 0.40H), 4.25 (d, J = 5.3 Hz, 1.59H), 4.08–3.99 (m, 0.19H), 3.91–3.77 (m, 0.84H), 3.38–2.95 (m, 4H), 2.00–1.72 (m, 4H)

N-(1-benzylpiperidin-4-yl)-4-(trifluoromethyl)benzamide
Identifier	13
¹H NMR (400 MHz, CDCl₃)	δ 7.85 (d, J = 8.2 Hz, 2H), 7.68 (d, J = 8.2 Hz, 2H), 7.35–7.30 (m, 4H), 7.29–7.24 (m, 1H), 6.08 (d, J = 7.6 Hz, 1H), 4.08–3.96 (m, 1H), 3.53 (s, 2H), 2.93–2.82 (m, 2H), 2.19 (dt, J = 11.8, 1.8 Hz, 2H), 2.08–1.98 (m, 3H), 1.60 (dq, J = 11.3, 3.7 Hz, 2H)
¹⁹F NMR (377 MHz, CDCl₃)	δ –62.9
¹³C NMR (151 MHz, CDCl₃)	δ 165.7, 138.0 (d, J = 46.3 Hz), 133.3 (q, J = 32.8 Hz), 129.4, 128.5, 127.5, 127.4, 125.7 (q, J = 3.8 Hz), 123.8 (q, J = 272.5 Hz), 63.1, 52.3, 47.4, 32.2
HRMS (ESI-TOF) m/z [M+H]⁺	calculated for C₂₀H₂₂F₃N₂O: 363.1679, found: 363.1677

13·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 10.90 (s, 0.80H), 10.72 (s, 0.18H), 8.83 (d, J = 7.4 Hz, 0.80H), 8.63 (d, J = 6.0 Hz, 0.17H), 8.11 (d, J = 8.1 Hz, 0.34H), 8.06 (d, J = 8.1 Hz, 1.65H), 7.89–7.80 (m, 2H), 7.68–7.60 (m, 2H), 7.51–7.42 (m, 3H), 4.33 (d, J = 5.6 Hz, 0.35H), 4.26 (d, J = 5.2 Hz, 1.59H), 4.22–4.13 (m, 0.21H), 4.10–3.93 (m, 0.84H), 3.40–2.98 (m, 4H), 2.15–1.90 (m, 4H)

2-(1-benzylpiperidin-4-yl)isoindolin-1-one
Identifier	14
¹H NMR (400 MHz, CDCl₃)	δ 7.84 (d, J = 7.9 Hz, 1H), 7.52 (dt, J = 7.4, 0.9 Hz, 1H), 7.47–7.42 (m, 2H), 7.36–7.30 (m, 4H), 7.30–7.23 (m, 1H), 4.36 (s, 2H), 4.30 (quin, J = 4.9 Hz, 1H), 3.55 (s, 2H), 3.07–2.94 (m, 2H), 2.19 (dt, J = 11.6, 3.2 Hz, 2H), 1.91–1.78 (m, 4H)
¹³C NMR (101 MHz, CDCl₃)	δ 168.2, 141.4, 138.3, 133.3, 131.2, 129.3, 128.4, 128.1, 127.2, 123.7, 122.9, 63.2, 53.0, 49.0, 46.2, 30.5
HRMS (ESI-TOF) [M+H]⁺	m/z: 307.1805 calculated for C₂₀H₂₃N₂O, found: 307.1800

14·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 11.16 (s, 1H), 7.77–7.55 (m, 5H), 7.55–7.41 (m, 4H), 4.70 (s, 0.16H), 4.54 (d, J = 6.0 Hz, 0.18H), 4.42 (s, 1.84H), 4.39–4.26 (m, 2.79H), 3.39 (d, J = 11.9 Hz, 2H), 3.15 (q, J = 10.5 Hz, 2H), 2.42–2.30 (m, 2H), 1.91 (d, J = 12.8 Hz, 2H)

2-(1-benzylpiperidin-4-yl)isoindoline-1,3-dione
Identifier	15
¹H NMR (400 MHz, CDCl₃)	δ 7.85–7.78 (m, 2H), 7.73–7.66 (m, 2H), 7.40–7.29 (m, 4H), 7.28–7.22 (m, 1H), 4.13 (tt, J = 12.4, 4.0 Hz, 1H), 3.56 (s, 2H), 3.07–2.94 (m, 2H), 2.57 (dq, J = 12.4, 4.0 Hz, 2H), 2.11 (dt, J = 12.2, 1.9 Hz, 2H), 1.71–1.60 (m, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 168.4, 138.6, 133.9, 132.1, 129.2, 128.3, 127.1, 123.2, 62.8, 53.3, 49.5, 29.1
HRMS (ESI-TOF) [M+H]⁺	m/z: 321.1598 calculated for C₂₀H₂₁N₂O₂, found: 321.1596

15·HCl
¹H NMR (400 MHz, MeOD-d₄)	δ 7.89–7.77 (m, 4H), 7.59–7.49 (m, 5H), 4.48 (tt, J = 12.2, 4.0 Hz, 1H), 4.36 (s, 2H), 3.66–3.52 (m, 2H), 3.21 (t, J = 12.2 Hz, 2H), 2.76 (dq, J = 13.7, 4.0 Hz, 2H), 2.10–1.99 (m, 2H)

Tert-Butyl 4-(2-phenylacetamido)piperidine-1-carboxylate
Identifier	SI-43
¹H NMR (400 MHz, CDCl₃)	δ 7.38–7.26 (m, 3H), 7.25–7.20 (m, 2H), 5.36–5.20 (m, 1H), 4.14–3.80 (m, 3H), 3.55 (s, 2H), 2.82 (t, J = 12.1 Hz, 2H), 1.86–1.77 (m, 2H), 1.42 (s, 9H), 1.17 (dq, J = 11.7, 4.3 Hz, 2H)

4-(2-phenylacetamido)piperidinium chloride
Identifier	SI-44
¹H NMR (400 MHz, MeOD-d₄)	δ 7.33–7.20 (m, 5H), 3.97–3.88 (m, 1H), 3.51 (s, 2H), 3.40 (dt, J = 13.3, 3.6 Hz, 2H), 3.08 (dt, J = 12.9, 2.9 Hz, 2H), 2.13–2.04 (m, 2H), 1.80–1.66 (m, 2H)

N-(1-(4-methoxybenzyl)piperidin-4-yl)-2-phenylacetamide
Identifier	16
¹H NMR (400 MHz, CDCl₃)	δ 7.37–7.26 (m, 3H), 7.26–7.15 (m, 4H), 6.86–6.80 (m, 2H), 5.20 (d, J = 7.8 Hz, 1H), 3.85–3.73 (m, 4H), 3.54 (s, 2H), 3.40 (s, 2H), 2.80–2.82 (m, 2H), 2.07 (t, J = 11.9 Hz, 2H), 1.88–1.88 (m, 2H), 1.39–1.23 (m, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 170.4, 158.9, 135.1, 130.4, 129.5, 129.2, 127.5, 113.7, 62.5, 55.4, 52.1, 46.5, 44.1, 32.1
HRMS (ESI-TOF) [M+H]⁺	m/z: 339.2067 calculated for C₂₁H₂₇N₂O₂, found: 339.2065

16·HCl
¹H NMR (400 MHz, MeOD-d₄)	δ 7.45–7.30 (m, 2H), 7.33–7.25 (m, 4H), 7.25–7.19 (m, 1H), 7.05–6.99 (m, 2H), 4.22 (s, 2H), 4.00–3.85 (m, 1H), 3.83 (s, 3H), 3.60–3.35 (m, 4H), 3.22–2.95 (m, 2H), 2.21–2.00 (m, 2H), 1.76 (br. s, 2H)

N-(1-(2-phenoxyethyl)piperidin-4-yl)-2-phenylacetamide
Identifier	17
¹H NMR (400 MHz, CDCl₃)	δ 7.38–7.31 (m, 2H), 7.31–7.21 (m, 5H), 6.96–6.91 (m, 1H), 6.90–6.85 (m, 2H), 5.21 (d, J = 7.7 Hz, 1H), 4.05 (t, J = 5.8 Hz, 2H), 3.87–3.74 (m, 1H), 3.55 (s, 2H), 2.89–2.79 (m, 2H), 2.76 (t, J = 5.8 Hz, 2H), 2.24 (dt, J = 11.8, 2.3 Hz, 2H), 1.92–1.82 (m, 2H), 1.44–1.28 (m, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 170.4, 158.8, 135.1, 129.6, 129.5, 129.2, 127.5, 120.9, 114.7, 66.0, 57.3, 52.8, 46.3, 44.1, 32.1, 29.8
HRMS (ESI-TOF) [M+H]⁺	m/z: 339.2067 calculated for C₂₁H₂₇N₂O₂, found: 339.2065

17·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 10.90 (s, 0.77H), 10.68 (s, 0.20H), 8.53 (d, J = 6.8 Hz, 0.19H), 8.36 (d, J = 7.4 Hz, 0.77H), 7.37–7.17 (m, 7H), 7.05–6.95 (m, 3H), 4.46–4.37 (m, 2H), 4.02–3.91 (m, 0.20H), 3.83–3.69 (m, 0.81H), 3.61–3.49 (m, 2.36H), 3.48–3.37 (m, 4H), 3.20–3.06 (m, 1.56H), 2.10–1.72 (m, 4H)

Tert-Butyl 4-(2-bromoacetamido)piperidine-1-carboxylate
Identifier	SI-48
¹H NMR (500 MHz, CDCl₃)	δ 6.39 (d, J = 7.1 Hz, 1H), 4.20–3.95 (m, 2H), 3.94–3.86 (m, 1H), 3.85 (s, 2H), 2.87 (t, J = 12.4 Hz, 2H), 1.94–1.86 (m, 2H), 1.44 (s, 9H), 1.36 (dq, J = 11.8, 4.3 Hz, 2H)

Tert-Butyl 4-(2-(3,5-dimethylphenoxy)acetamido)piperidine-1-carboxylate
Identifier	SI-50
¹H NMR (400 MHz, CDCl₃)	δ 6.67 (m, 0.88H), 6.53 (s, 2H), 6.51–6.44 (m, 1.38H), 4.44 (s, 1.83H), 4.12–3.94 (m, 3H), 3.86 (s, 0.18H), 2.88 (t, J = 12.2 Hz, 2H), 2.29 (s, 5H), 2.25 (s, 1H), 1.96–1.86 (m, 2H), 1.45 (s, 9H), 1.36 (dq, J = 12.2, 4.2 Hz, 2H)

Tert-Butyl 4-(N-benzyl-2-(3,5-dimethylphenoxy)acetamido)piperidine-1-carboxylate
Identifier	SI-51
¹H NMR (400 MHz, CDCl₃)	δ 7.40–7.26 (m, 2H), 7.26–7.10 (m, 3H), 6.66 (s, 0.39H), 6.59 (s, 1.36H), 6.43 (s, 1.18H), 4.80 (s, 0.78H), 4.67–4.49 (m, 3.79H), 4.31–3.99 (m, 2.42H), 2.81–2.60 (m, 2H), 2.29 (s, 2.39H), 2.24 (s, 3.61H), 1.73–1.46 (m, 4.85H), 1.46–1.40 (m, 9H), 1.32–1.24 (m, 0.22H)

N-benzyl-2-(3,5-dimethylphenoxy)-N-(piperidin-4-yl)acetamide
Identifier	18
¹H NMR (400 MHz, CDCl₃)	δ 7.40–7.10 (m, 5H), 6.70–6.55 (m, 2H), 6.43 (s, 1H), 4.79 (s, 1H), 4.65–4.51 (m, 3.59H), 3.99 (quin, J = 7.0 Hz, 0.47H), 3.15–3.00 (m, 2H), 2.74–2.54 (m, 2H), 2.29 (s, 2.88H), 2.24 (s, 3.27H), 1.72–1.50 (m, 5H)
¹³C NMR (101 MHz, CDCl₃)	δ 168.8, 168.6, 158.2, 158.1, 139.6, 139.3, 138.9, 138.2, 128.9, 128.4, 127.5, 127.0, 126.8, 126.1, 123.6, 123.4, 112.6, 112.5, 68.4, 67.7, 56.3, 53.3, 46.5, 46.3, 46.3, 45.2, 32.7, 30.9, 21.6, 21.5
HRMS (ESI-TOF) [M+H]⁺	m/z: 353.2224 calculated for C₂₂H₂₉N₂O₂, found: 353.2222

18·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 9.18–8.60 (m, 2H), 7.45–7.15 (m, 5H), 6.64–5.51 (m, 2.24H), 6.37 (s, 0.74H), 5.00 (s, 1.21H), 4.65–4.54 (m, 1.47H), 4.54–4.36 (m, 1.63H), 4.20–4.06 (m, 0.63H), 3.31–3.21 (m, 2H), 3.01–2.82 (m, 2H), 2.24 (s, 3.75H), 2.18 (s, 2.27H), 2.09–1.89 (m, 2H), 1.85–1.66 (m, 2H)

N-(1-(4-phenoxybenzyl)piperidin-4-yl)acetamide
Identifier	19
¹H NMR (400 MHz, CDCl₃)	δ 7.36–7.29 (m, 2H), 7.29–7.22 (m, 2H), 7.09 (tt, J = 7.3, 1.1 Hz, 1H), 7.03–6.98 (m, 2H), 6.97–6.92 (m, 2H), 5.52–5.27 (m, 1H), 3.88–3.72 (m, 1H), 3.47 (s, 2H), 2.90–2.75 (m, 2H), 2.12 (dt, J = 11.8, 1.8 Hz, 2H), 1.96 (s, 3H), 1.95–1.85 (m, 2H), 1.46 (dq, J = 11.4, 3.7 Hz, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.5, 157.4, 156.4, 133.0, 130.6, 129.8, 123.3, 118.9, 118.8, 62.5, 52.3, 46.7, 32.4, 23.7
HRMS (ESI-TOF) [M+H]⁺	m/z: 325.1911 calculated for C₂₀H₂₅N₂O, found: 325.1907

19·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 11.03 (s, 0.8H), 10.86 (s, 0.2H), 8.21 (d, J = 6.8 Hz, 0.19H), 8.07 (d, J = 7.4 Hz, 0.79H), 7.67–7.59 (m, 2H), 7.46–7.38 (m, 2H), 7.18 (tt, J = 7.4, 1.0 Hz, 1H), 7.09–7.00 (m, 4H), 5.50 (br. s, H₂O, NH, 4.45H), 4.25 (d, J = 5.5 Hz, 0.4H), 4.20 (d, J = 5.2 Hz, 1.57H), 3.99–3.90 (m, 0.2H), 3.79–3.64 (m, 0.8H), 3.36–3.06 (m, 2.38H), 3.05–2.87 (m, 1.6H), 2.09–1.72 (m, 7H)

Tert-Butyl 5-(benzofuran-2-carbonyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate
Identifier	SI-56
¹H NMR (400 MHz, CDCl₃)	δ 7.70–7.64 (m, 1H), 7.53 (d, J = 8.3 Hz, 1H), 7.45 (d, J = 1.0 Hz, 1H), 7.41 (ddd, J = 8.3, 6.0, 1.3 Hz, 1H), 7.32–7.27 (m, 1H), 4.35–4.13 (m, 1H), 4.09–3.80 (m, 2H), 3.80–3.53 (m, 2H), 3.51–3.14 (m, 2H), 3.12–2.82 (m, 2H), 1.46 (s, 9H)

Benzofuran-2-yl(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone
Identifier	20
¹H NMR (400 MHz, CDCl₃)	δ 7.67–7.61 (m, 1H), 7.54–7.48 (m, 1H), 7.41–7.35 (m, 2H), 7.29–7.23 (m, 1H), 4.26–4.05 (m, 1H), 4.05–3.89 (m, 1H), 3.89–3.75 (m, 1H), 3.75–3.54 (m, 1H), 3.13 (dd, J = 11.2, 7.2 Hz, 2H), 3.03–2.73 (m, 4H), 2.28 (s, 1H)
¹³C NMR (101 MHz, CDCl₃)	δ 158.6, 155.0, 149.6, 127.1, 126.7, 123.7, 122.5, 112.2, 112.0, 53.3, 52.9, 52.1, 44.7, 41.5 (different conformers)
HRMS (ESI-TOF) [M+H]⁺	m/z: 363.1679 calculated for C₂₀H₂₂F₃N₂O, found: 363.1677

20·HCl
¹H NMR (400 MHz, MeOD-d₄)	δ 7.79–7.74 (m, 1H), 7.64–7.59 (m, 1H), 7.55 (d, J = 0.9 Hz, 1H), 7.49 (ddd, J = 8.4, 7.2, 1.3 Hz, 1H), 7.39–7.32 (m, 1H), 4.46–4.22 (m, 1H), 4.22–4.06 (m, 1H), 4.06–3.90 (m, 1H), 3.90–3.72 (m, 1H), 3.65 (d, J = 7.8 Hz, 1H), 3.62 (d, J = 7.8 Hz, 1H), 3.42–3.18 (m, 4H)

Ethyl 4-methyl-2-phenylthiazole-5-carboxylate
Identifier	SI-59
¹H NMR (400 MHz, CDCl₃)	δ 8.00–7.90 (m, 2H), 7.50–7.37 (m, 3H), 4.35 (q, J = 7.1 Hz, 2H), 2.78 (s, 3H), 1.39 (t, J = 7.1 Hz, 3H)

4-methyl-2-phenylthiazole-5-carboxylic acid
Identifier	SI-60
¹H NMR (400 MHz, CDCl₃)	δ 13.39 (br. s, 1H), 8.03–7.92 (m, 2H), 7.60–7.46 (m, 3H), 2.67 (s, 3H)

4-methyl-2-phenyl-N-((1R,3S,4R)-quinuclidin-3-yl)thiazole-5-carboxamide
Identifier	21
¹H NMR (400 MHz, CDCl₃)	δ 7.98–7.89 (m, 2H), 7.50–7.39 (m, 3H), 5.93 (d, J = 6.5 Hz, 1H), 4.17–4.07 (m, 1H), 3.48–3.41 (m, 1H), 2.97–2.77 (m, 4H), 2.75 (s, 3H), 2.59 (ddd, J = 14.3, 4.9, 2.0 Hz, 1H), 2.04 (sex, J = 3.2 Hz, 1H), 1.78–1.66 (m, 3H), 1.61–1.50 (m, 1H)
¹³C NMR (101 MHz, CDCl₃)	δ 167.3, 161.9, 156.1, 133.0, 131.0, 129.2, 126.9, 125.9, 56.5, 47.7, 47.6, 46.8, 25.9, 25.9 (HSQC), 20.5, 17.6
HRMS (ESI-TOF) [M+H]⁺	m/z: 328.1478 calculated for C₁₈H₂₂N₃OS, found: 328.1476

21·HCl
¹H NMR (400 MHz, MeOD-d₄)	δ 8.03–7.97 (m, 2H), 7.63–7.52 (m, 3H), 4.55–4.38 (m, 1H), 3.83 (dt, J = 10.0, 2.5 Hz), 3.54–3.43 (m, 1H), 3.43–3.31 (m, 4H), 2.73 (s, 3H), 2.41–2.35 (m, 1H), 2.31–2.18 (m, 1H), 2.16–2.05 (m, 2H), 2.02–1.91 (m, 1H)

5-methoxy-1-methyl-2H-benzo[d][1,3]oxazine-2,4(1H)-dione
Identifier	SI-63
¹H NMR (400 MHz, CDCl₃)	δ 7.66 (t, J = 8.5 Hz, 1H), 6.79 (d, J = 8.5 Hz, 1H), 6.73 (d, J = 8.5 Hz, 1H), 4.00 (s, 3H), 3.54 (s, 3H)

6-methoxy-1-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione
Identifier	SI-64
¹H NMR (400 MHz, CDCl₃)	δ 7.42 (t, J = 8.4 Hz, 1H), 6.92 (t, J = 6.4 Hz, 1H), 6.86 (d, J = 8.4 Hz, 1H), 6.81 (d, J = 8.4 Hz, 1H), 3.92 (s, 3H), 3.88 (dd, J = 15.0, 7.2 Hz, 1H), 3.69 (dd, J = 15.0, 6.4 Hz, 1H), 3.35 (s, 3H)

6-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine
Identifier	SI-65
¹H NMR (400 MHz, CDCl₃)	δ 7.18–7.10 (m, 1H), 6.61–6.47 (m, 2H), 4.83 (br. s, 1H), 4.13 (s, 1.51H), 4.04 (s, 0.48H), 3.79 (s, 2.33H), 3.73 (s, 0.74H), 3.15–2.99 (m, 4H), 2.90 (s, 2.24H), 2.88 (s, 0.85H)

4-(cyclohexylmethyl)-6-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine
Identifier	22
¹H NMR (400 MHz, CDCl₃)	δ 7.14 (t, J = 8.2 Hz, 1H), 6.56–6.49 (m, 2H), 3.92 (br. s, 2H), 3.79 (s, 3H), 3.05 (br. s, 2H), 2.87 (m, 5H), 2.24 (d, J = 6.4 Hz, 2H), 1.88–1.76 (m, 2H), 1.76–1.57 (m, 4H), 1.32–1.10 (m, 3H), 0.94–0.80 (m, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 158.5, 154.0 (HMBC), 128.1, 117.9 (HMBC), 108.7, 103.9, 62.1, 56.9, 55.8, 54.5, 49.0, 42.8, 35.8, 32.1, 26.9, 26.4
HRMS (ESI-TOF) [M+H]⁺	m/z: 289.2274 calculated for C₁₈H₂₉N₂O, found: 289.2269

22·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 10.38 (br. s, 1H), 7.32 (t, J = 8.3 Hz, 1H), 6.68 (d, J = 8.3 Hz, 1H), 6.62 (d, J = 8.3 Hz, 1H), 4.31 (d, J = 13.6 Hz, 1H), 4.24 (dd, J = 13.6, 3.6 Hz, 1H), 3.81 (s, 3H), 3.61–3.49 (m, 1H), 3.44–3.34 (m, 1H), 3.22–3.06 (m, 2H), 2.84 (s, 3H), 2.83–2.77 (m, 2H), 1.97 (d, J = 12.7 Hz, 1H), 1.93–1.79 (m, 1H), 1.79–1.58 (m, 4H), 1.35–1.05 (m, 3H), 1.05–0.87 (m, 2H)

1-(bromomethyl)-2-methoxynaphthalene
Identifier	SI-68
¹H NMR (400 MHz, CDCl₃)	δ 8.03 (d, J = 8.7 Hz, 1H), 7.86 (d, J = 9.0 Hz, 1H), 7.81 (d, J = 8.3 Hz, 1H), 7.60 (ddd, J = 8.3, 6.9, 1.4 Hz, 1H), 7.39 (ddd, J = 8.0, 6.9, 1.0 Hz, 1H), 7.26 (d, J = 9.0 Hz, 1H), 5.10 (s, 2H), 4.03 (s, 3H)

Tert-Butyl (3-(((2-methoxynaphthalen-1-yl)methyl)(methyl)amino)propyl)carbamate
Identifier	SI-70
¹H NMR (400 MHz, CDCl₃)	δ 8.14 (d, J = 8.6 Hz, 1H), 7.80 (d, J = 9.1 Hz, 1H), 7.77 (d, J = 8.4 Hz, 1H), 7.49 (ddd, J = 8.4, 6.9, 1.4 Hz, 1H), 7.34 (ddd, J = 7.9, 6.9, 1.0 Hz, 1H), 7.28 (d, J = 9.1 Hz, 1H), 5.12–4.34 (m, 1H), 4.01–3.81 (m, 5H), 3.13–2.94 (m, 2H), 2.60–2.44 (m, 2H), 2.25 (s, 3H), 1.67 (quin, J = 6.3 Hz, 2H), 1.38 (s, 9H)

N1-((2-methoxynaphthalen-1-yl)methyl)-N1-methylpropane-1,3-diamine
Identifier	SI-71
¹H NMR (400 MHz, CDCl₃)	δ 8.18 (d, J = 8.7 Hz, 1H), 7.81–7.72 (m, 2H), 7.48 (ddd, J = 8.3, 6.8, 1.3 Hz, 1H), 7.33 (ddd, J = 8.0, 6.8, 1.0 Hz, 1H), 7.26 (d, J = 9.1 Hz, 1H), 3.94 (s, 3H), 2.93 (s, 2H), 2.67 (t, J = 6.8 Hz, 2H), 2.53 (t, J = 7.0 Hz, 2H), 2.23 (s, 3H), 1.68 (quin, J = 6.8 Hz, 2H), 1.48–1.36 (m, 2H)

N-(1-((2-methoxynaphthalen-1-yl)methyl)-N-methylpropyl)cyclobutanecarboxamide
Identifier	23
¹H NMR (400 MHz, CDCl₃)	δ 8.10 (d, J = 8.6 Hz, 1H), 7.87–7.77 (m, 2H), 7.49 (ddd, J = 8.2, 6.8, 1.3 Hz, 1H), 7.36 (ddd, J = 8.1, 6.8, 1.0 Hz, 1H), 7.29 (d, J = 9.2 Hz, 1H), 6.40 (br. s, 1H), 3.96 (br. s, 2H), 3.94 (s, 2H), 3.21 (q, J = 5.7 Hz, 2H), 2.56 (t, J = 5.8 Hz, 2H), 2.38–2.28 (m, 1H), 2.26 (s, 3H), 1.98–1.85 (m, 2H), 1.78–1.55 (m, 6H)
¹³C NMR (101 MHz, CDCl₃)	δ 174.6, 155.7, 133.8, 129.5, 129.2, 128.5, 126.6, 123.8, 123.5, 120.0, 113.2, 56.5, 55.8, 52.2, 41.4, 39.8, 38.7, 25.5, 25.1, 18.0
HRMS (ESI-TOF) [M+H]⁺	m/z: 341.2224 calculated for C₂₁H₂₉N₂O₂, found: 341.2220

23·HCl
¹H NMR (400 MHz, MeOD-d₄)	δ 8.17–8.07 (m, 2H), 7.98–7.89 (m, 1H), 7.65 (ddd, J = 8.4, 6.9, 1.3 Hz, 1H), 7.55 (d, J = 9.2 Hz, 1H), 7.45 (ddd, J = 8.0, 6.9, 0.9 Hz, 1H), 4.99–4.89 (m, 1H), 4.82–4.70 (m, 1H), 4.10 (s, 3H), 3.47–3.18 (m, 5H), 3.07 (dquin, J = 8.6, 1.0 Hz, 1H), 2.79 (s, 3H), 2.27–1.91 (m, 7H), 1.88–1.75 (m, 1H)

2-(3-(isoindolin-2-yl)propyl)isoindoline-1,3-dione
Identifier	24
¹H NMR (400 MHz, CDCl₃)	δ 7.84–7.77 (m, 2H), 7.69–7.62 (m, 2H), 7.18–7.12 (m, 4H), 3.92–3.88 (m, 4H), 3.83 (t, J = 7.2 Hz, 2H), 2.81 (t, J = 7.2 Hz, 2H), 1.95 (quin, J = 7.2 Hz, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 168.6, 140.1, 133.9, 132.3, 126.7, 123.2, 122.3, 59.0, 53.5, 36.4, 27.8
HRMS (ESI-TOF) [M+H]⁺	m/z: 307.1440 calculated for C₁₉H₁₉N₂O₂, found: 307.1438

24·HCl
¹H NMR (400 MHz, DMSO-d₆)	δ 11.83 (br. s, 1H), 7.92–7.82 (m, 4H), 7.41–7.32 (m, 4H), 4.73 (d, J = 13.7 Hz, 2H), 4.46 (d, J = 13.7 Hz, 2H), 3.69 (t, J = 6.5 Hz, 2H), 3.47–3.38 (m, 2H), 2.16–2.05 (m, 2H)

2-(3-(methyl(phenethyl)amino)propyl)isoindoline-1,3-dione
Identifier	25
¹H NMR (400 MHz, CDCl₃)	δ 7.87–7.82 (m, 2H), 7.73–7.68 (m, 2H), 7.27 (t, J = 7.5 Hz, 2H), 7.24–7.18 (m, 3H), 3.73 (t, J = 7.2 Hz, 2H), 2.75–2.69 (m, 2H), 2.61–2.56 (m, 2H), 2.48 (t, J = 7.1 Hz, 2H), 2.28 (s, 3H), 1.63 (quin, J = 7.1 Hz, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 168.5, 140.6, 134.0, 132.4, 128.8, 126.1, 123.3, 59.7, 55.2, 42.1, 36.6, 33.9, 26.4
HRMS (ESI-TOF) [M+H]⁺	m/z: 323.1754 calculated for C₂₀H₂₃N₂O₂, found: 323.1751

25·HCl
¹H NMR (400 MHz, MeOD-d₄)	δ 7.92–7.86 (m, 2H), 7.86–7.80 (m, 2H), 7.37–7.22 (m, 5H), 3.80 (t, J = 6.6 Hz, 2H), 3.43–3.35 (m, 2H), 3.30–3.23 (m, 2H), 3.09–3.02 (m, 2H), 2.94 (s, 3H), 2.18–2.09 (m, 2H)