1-(4-Chlorophenyl)cyclohexanecarboxylic acid → N-(3-{4-[3-(acetylamino)phenyl]-1-piperidinyl}propyl)-1-(4-chlorophenyl)cyclohexanecarboxamide
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:36])[CH3:35])[CH:30]=[CH:31][CH:32]=2)[CH2:23][CH2:22]1>>[C:34]([NH:33][C:29]1[CH:28]=[C:27]([CH:24]2[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][CH2:18][NH:17][C:14]([C:8]3([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]3)=[O:16])[CH2:22][CH2:23]2)[CH:32]=[CH:31][CH:30]=1)(=[O:36])[CH3:35]Participants
3
Procedure
Example 75 was prepared from 1-(4-chlorophenyl) cyclohexanecarboxylic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}acetamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 7.47 (s, 1H), 7.44 (s, 1H), 7.40–7.37 (m, 2H), 7.32–7.25 (m, 4H), 6.96 (d, 1H, J=7.2 Hz), 6.81 (br s, 1H), 3.30 (dd, 2H, J=5.6, 11.6 Hz), 2.94 (d, 2H, J=12.4 Hz), 2.49 (m, 1H), 2.34 (t, 4H, J=6.4 Hz), 2.20 (s, 3H), 1.99–1.81 (m, 6H), 1.72–1.55 (m, 10H); ESMS m/e: 496.2 (M+H)+.
Sources & evidence
- ORD record
- ord-ba40cad845114161a539496368f5ccd0
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199135B2
Reaction notes
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