1-(p-Chlorophenyl)cyclopropanecarboxylic acid → N-(3-{4-[3-(butyrylamino)phenyl]-1-piperidinyl}propyl)-1-(4-chlorophenyl)cyclopropanecarboxamide
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](=[O:35])[CH2:32][CH2:33][CH3:34])[CH:27]=[CH:28][CH:29]=2)[CH2:20][CH2:19]1>>[C:31]([NH:30][C:26]1[CH:25]=[C:24]([CH:21]2[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH2:15][NH:14][C:11]([C:8]3([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[CH2:9][CH2:10]3)=[O:13])[CH2:19][CH2:20]2)[CH:29]=[CH:28][CH:27]=1)(=[O:35])[CH2:32][CH2:33][CH3:34]Participants
3
Procedure
Example 69 was prepared from 1-(4-chlorophenyl) cyclopropanecarboxylic acid and N{3-[1-(3-amino propyl)-4-piperidinyl]phenyl}butanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H), 7.45 (s, 1H), 7.36–7.34 (m, 5H), 7.24 (t, 1H, J=8.0 Hz), 6.94 (d, 1H, J=7.6 Hz), 5.69 (br s, 1H), 3.25 (dd, 2H, J=6.8, 12.8 Hz), 2.87 (d, 2H, J=11.6 Hz), 2.44 (m, 1H), 2.35 (t, 2H, J=7.2 Hz), 2.29 (t, 2H, J=6.8 Hz), 1.95 (t, 2H, J=11.2 Hz), 1.80–1.74 (m, 4H), 1.63–1.59 (m, 6H), 1.03–1.00 (m, 5H); ESMS m/e: 482.3 (M+H)+.
Sources & evidence
- ORD record
- ord-06ebf5db8d794968bb9b2d2d46860b70
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199135B2
Reaction notes
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