1-(2-Methoxyphenyl)piperazine → 1-{3-[5-Chloro-2-(4-chlorophenyl)-1H-indol-3-yl]-1-oxopropyl}-4-(2-methoxyphenyl)piperazine
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[C:5]2[CH2:18][CH2:19][C:20](O)=[O:21].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)=[C:5]2[CH2:18][CH2:19][C:20]([N:34]1[CH2:33][CH2:32][N:31]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[O:24][CH3:23])[CH2:36][CH2:35]1)=[O:21]Participants
3
Procedure
Prepared from 5-chloro-2-(4-chlorophenyl)-1H-indole-3-propanoic acid (Description 30) and 1-(2-methoxyphenyl)piperazine according to the method of Description 32. 1H NMR (250 MHz, CDCl3) δ 8.04 (1H, br s), 7.61 (1H, d, J 1.8 Hz), 7.48 (4H, m), 7.29 (1H, d, J 8.5 Hz), 7.17 (1H, dd, J 8.5, 1.8 Hz), 7.02 (1H, m), 7.00-6.82 (3H, m), 3.86 (3H, s), 3.78 (2H, t, J 4.9 Hz), 3.46 (2H, t, J 4.9 Hz), 3.24 (2H, t, J 7.9 Hz), 2.94 (2H, t, J 4.9 Hz), 2.79 (2H, t, J 4.9 Hz), and 2.68 (2H, t, J 7.9 Hz). m/z (ES+) 508, 510 (M+1).
Sources & evidence
- ORD record
- ord-4cc26ddf84614ad1932c76eeaf7054b6
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06476045B2
Reaction notes
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