4-(2-Methylsulfinyl-3-pyridyl)piperidine → 3-[1-(3,4-Dichlorophenyl)-3-(4-(2-methylsulfinyl-3-pyridyl)piperidino)propyl]-6-methoxy-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][C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[C:15](=[O:24])[N:14]2[CH3:25])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:26][S:27]([C:29]1[C:34]([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[CH:33][CH:32]=[CH:31][N:30]=1)=[O:28]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[C:15](=[O:24])[N:14]2[CH3:25])[CH2:10][CH2:11][N:38]2[CH2:39][CH2:40][CH:35]([C:34]3[C:29]([S:27]([CH3:26])=[O:28])=[N:30][CH:31]=[CH:32][CH:33]=3)[CH2:36][CH2:37]2)[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
3
Reactant 2
Product 1
Procedure
3-(3,4-Dichlorophenyl)-3-(5-methoxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.33 g) was coupled to 4-(2-methylsulfinyl-3-pyridyl)piperidine (0.423 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 (0.26 g); mp 120°-182° C. (d); MS: m/z=586(M+1); NMR(CD3OD): 2.0-2.3 (m,4), 2.6 (m,2), 2.9 (m,5), 3.2-3.3 (m,4), 3.6-3.9 (m,8), 4.8 (m,1), 6.7-7.3 (m,5), 7.5-8.1 (m,3), 8.7 (broad,1). Analysis for C30 H33Cl2N3O3S.2.0 HCl.1.0 H2O: Calculated: C, 53.18; H, 5.50, N, 6.20; Found: C, 53.39; H, 4.49; N, 6.53.
Workup
- customThe reaction product was purified by chromatography
Sources & evidence
- ORD record
- ord-a423a411b264458392c0e6a385844a28
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05705505
Reaction notes
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