3-(3,4-dichlorophenyl)-3-(2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde → 3-[1-(3,4-Dichlorophenyl)-3-(4-(2-methylsulfonylphenyl)piperidino)propyl]-2-ethyl-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[CH2:23][CH3:24])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:25][S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)(=[O:28])=[O:27]>>[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[CH2:23][CH3:24])[CH2:10][CH2:11][N:38]2[CH2:37][CH2:36][CH:35]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[S:26]([CH3:25])(=[O:28])=[O:27])[CH2:40][CH2:39]2)[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
3
Reactant 2
Product 1
Procedure
3-(3,4-Dichlorophenyl)-3-(2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl) propionaldehyde (0.724 g) was coupled to 4-(2-methylsufonyl-phenyl)piperidine (0.706 g) by a method similar to that described in Example 8. The reaction product was not purified by chromatography but converted to the hydrochloride salt to afford the title compound (0.64 g); mp 168°-175° C. (d); MS: m/z=585(M+1); NMR (CDCl3): 1.19 (m,3), 2.0 (m,3), 2.35 (m,7), 2.95 (s,3), 4.87 (m, 1), 6.56-8.01 (m, 11). Analysis for C31H34Cl2N2O3S·1.5 HCl·1.5 H2O: Calculated: C, 55.79; H, 5.82, N, 4.20; Found: C, 55.90; H, 5.45; N, 4.20.
Workup
- customThe reaction product was not purified by chromatography
Sources & evidence
- ORD record
- ord-c9e85be794cf495d9a5ee906699780f5
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05589489
Reaction notes
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