2-(4-Chlorophenyl)-2-methylpropionic acid → 2-(4-chlorophenyl)-2-methyl-N-(3-{4-[3-(propionylamino)phenyl]-1-piperidinyl}propyl)propanamide

HRID 2213381Notes

Reaction equation

HRID 2213381 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:25]=[C:26]([NH:30][C:31](=[O:34])[CH2:32][CH3:33])[CH:27]=[CH:28][CH:29]=2)[CH2:20][CH2:19]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([NH:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31](=[O:34])[CH2:32][CH3:33])[CH:25]=3)[CH2:20][CH2:19]2)=[O:11])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 804062-(4-Chlorophenyl)-2-methylpropionic acidHCID 21957142N-{3-[1-(3-aminopropyl)4-piperidinyl]phenyl}propanamide

Product 1

HCID 103674292-(4-chlorophenyl)-2-methyl-N-(3-{4-[3-(propionylamino)phenyl]-1-piperidinyl}propyl)propanamide

Procedure

Example 7 was prepared from 2-(4-chlorophenyl)-2-methylpropanoic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}propanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 7.86 (s, 1H), 7.50 (s, 1H), 7.34–7.19 (m, 6H), 6.96 (d, 1H, J=7.8 Hz), 6.72–6.67 (m, 1H), 3.42 (q, 2H, J=7.1 Hz), 3.31 (q, 3H, J=5.4 Hz), 2.49–2.35 (m, 5H), 2.08–1.95 (m, 2H), 1.82–1.74 (m, 2H), 1.71–1.62 (m, 3H), 1.56 (s, 6H), 1.24 (t, 3H, J=7.8 Hz); ESMS m/e: 470.3 (M+H)+.

Sources & evidence

ORD record
ord-60cd485f5ee8470fa2d5418941b9c18e
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

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