N-(4-Phenylpiperidin-4-yl)acetamide → 3-[1-(3,4-Dichlorophenyl)-3-(4-acetamido-4-phenylpiperidino)propyl]-7-hydroxy-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](=[C:17]([OH:22])[CH:18]=[CH:19][CH:20]=3)[C:15](=[O:23])[N:14]2[CH3:24])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:25]([NH:28][C:29]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=[O:27])[CH3:26]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[C:17]([OH:22])[CH:18]=[CH:19][CH:20]=3)[C:15](=[O:23])[N:14]2[CH3:24])[CH2:10][CH2:11][N:32]2[CH2:33][CH2:34][C:29]([NH:28][C:25](=[O:27])[CH3:26])([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:30][CH2:31]2)[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
3
Reactant 2
Product 1
Procedure
3-(3,4-Dichlorophenyl)-3-(4-hydroxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.2.0 g) was coupled to 4-acetamido-4-phenylpiperidine (0.14 g) by a method similar to that described in Example 8. The reaction product was purified by chromatography and converted to the corresponding hydrochloride salt as described in the Example 8 to afford the title compound (0.27 g); mp 185°-205° C.; MS: m/z=566(M+1); NMR(CD3SOCD3): 2.88 (m,1), 2.96 (s,3), 4.79 (d,1, J=3.5), 6.86 (m,2), 7.09 (d,1, J=1.8), 7.20-7.47 (m,8). Analysis for C31H33Cl2N3 O2.1.0 HCl. 1.5 H2O: Calculated: C, 59.10; H, 5.91, N, 6.67; Found: C, 59.51; H, 5.63; N, 6.23.
Workup
- customThe reaction product was purified by chromatography
Sources & evidence
- ORD record
- ord-854c64d209ea4e009cd2ce123910fcfb
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05705505
Reaction notes
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