1-(4-Chlorophenyl)cyclohexanecarboxylic acid → 1-(4-chlorophenyl)-N-(3-{4-[3-(isobutyrylamino)phenyl]-1-piperidinyl}propyl)cyclohexanecarboxamide

HRID 1269223Notes

Reaction equation

HRID 1269223 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]([OH:16])=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([C:27]2[CH:28]=[C:29]([NH:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH:30]=[CH:31][CH:32]=2)[CH2:23][CH2:22]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:14]([NH:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34](=[O:38])[CH:35]([CH3:36])[CH3:37])[CH:28]=4)[CH2:23][CH2:22]3)=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1008731-(4-Chlorophenyl)cyclohexanecarboxylic acidHCID 16757470N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}2-methylpropanamide

Product 1

HCID 219571901-(4-chlorophenyl)-N-(3-{4-[3-(isobutyrylamino)phenyl]-1-piperidinyl}propyl)cyclohexanecarboxamide

Procedure

Example 45 was prepared from 1-(4-chloro phenyl) cyclohexanecarboxylic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}-2-methyl propanamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 7.57 (s, 1H), 7.52 (s, 1H), 7.38–7.35 (m, 2H), 7.30–7.21 (m, 4H), 6.93 (d, 1H, J=7.2 Hz), 6.88–6.83 (m, 1H), 3.28 (q, 2H, J=5.6 Hz), 2.95–2.88 (m, 2H), 2.56–2.41 (m, 2H), 2.35–2.26 (m, 3H), 2.07 (s, 1H), 1.96–1.84 (m, 4H), 1.83–1.76 (m, 2H), 1.70–1.53 (m, 10H), 1.24 (d, 6H, J=7.1 Hz); ESMS m/e: 524.3 (M+H)+.

Sources & evidence

ORD record
ord-6b6fd7c777f64914b796320d3df6c535
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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