1-(p-Chlorophenyl)cyclopropanecarboxylic acid → 1-(4-chlorophenyl)-N-[3-(4-{3-[(cyclopropylcarbonyl)amino]phenyl}-1-piperidinyl)propyl]cyclopropanecarboxamide

HRID 1269294Notes

Reaction equation

HRID 1269294 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[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]([CH:33]3[CH2:35][CH2:34]3)=[O:32])[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]2([C:11]([NH:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]([CH:33]5[CH2:35][CH2:34]5)=[O:32])[CH:25]=4)[CH2:20][CH2:19]3)=[O:13])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 986061-(p-Chlorophenyl)cyclopropanecarboxylic acidHCID 21957166N-{3-[1-(3-aminopropyl)4-piperidinyl]phenyl}cyclopropanecarboxamide

Product 1

HCID 219572121-(4-chlorophenyl)-N-[3-(4-{3-[(cyclopropylcarbonyl)amino]phenyl}-1-piperidinyl)propyl]cyclopropanecarboxamide

Procedure

Example 118 was prepared from 1-(4-chlorophenyl)cyclopropanecarboxylic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}cyclopropanecarboxamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 8.12–7.88 (br, 1H), 7.48–7.14 (m, 7H), 6.85 (d, 1H, J=7.2 Hz), 5.83–5.66 (br, 1H), 3.29–3.09 (m, 4H), 2.66–2.53 (m, 2H), 2.53–2.40 (m, 1H), 2.37–2.17 (m, 2H), 1.95–1.53 (m, 7H), 1.14–0.91 (m, 6H), 0.89–0.71 (m, 2H); ESMS m/e: 480.2 (M+H)+; Anal. Calc. (HCl salt) C28H35Cl2N3O2.0.38CHCl3: C, 60.64; H, 6.34; N, 7.47. Found: C, 60.38; H, 6.57; N, 7.80.

Sources & evidence

ORD record
ord-2eaa9a8472fe45ebaae3446835b387c6
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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