4-(2-Methoxyphenyl)piperidine → 3-[1-(3,4-Dichlorophenyl)-3-(4-(2-methoxyphenyl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]2[CH3:23])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]2[CH3:23])[CH2:10][CH2:11][N:35]2[CH2:36][CH2:37][CH:32]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[O:25][CH3:24])[CH2:33][CH2:34]2)[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
3
Procedure
3-(3,4-Dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.368 g) was coupled to 4-(2-methoxyphenyl)piperidine (0.203 g) by a method similar to that described in Example 8. The reaction product was not purified by chromatography but converted to the corresponding hydrochloride salt as described in Example 8 to afford the desired title compound (0.469 g); mp 175°-182° C.; MS: m/z=523(M+1); NMR(CD3SOCD3): 1.83-1.90 (m,3), 2.05-2.13 (m,2), 2.80 m(1), 3.07 (s,3), 3.57 (m,2), 3.8 (s,3), 4.89 (d,1, J=3.7), 6.7 (dd,1, J=8.4, 2), 7.0 (m,3), 7.12-7.6 (m,6), 7.94 (d,1, J=7.5). Analysis for C30 H32Cl2N2O2.1.0 HCl.5 H2O: Calculated: C, 61.39; H, 6.18, N, 4.77; Found: C, 61.33; H, 6.12; N, 4.99.
Workup
- customThe reaction product was not purified by chromatography
Sources & evidence
- ORD record
- ord-b04fc1fc89f1407f9774085491e4b1ba
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05705505
Reaction notes
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