4-(2-(Methylsulfinyl)phenyl)piperidine → 3-[1-(3,4-Dichlorophenyl)-3-(4-(2-methylsulfinylphenyl)piperidino)propyl]-6-methoxy-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

HRID 1082205Notes

Reaction equation

HRID 1082205 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[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]>>[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:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[S:27]([CH3:26])=[O:28])[CH2:36][CH2:37]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 187003874-(2-(Methylsulfinyl)phenyl)piperidineHCID 218397523-(3,4-Dichlorophenyl)-3-(5-methoxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde

Product 1

HCID 218399613-[1-(3,4-Dichlorophenyl)-3-(4-(2-methylsulfinylphenyl)piperidino)propyl]-6-methoxy-2-methyl-2,3-dihydroisoindol-1-one hydrochlorideYield 143.1%

Procedure

3-(3,4-Dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-5-methoxy-1H-isoindol-1-yl)propionaldehyde (0.38 g) was coupled to 4-(2-methylsulfinylphenyl)piperidine (0.29 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 Example 8 to afford the title compound (0.447 g); mp 155°-178° C. (d); MS: m/z=585(M+1); NMR(CD3OD): 2.0-2.3 (m,4), 2.6 (m,2), 2.8-3.0 (m,3), 3.0-3.3 (m,7), 3.5-3.8 (m,4), 3.85 (s,3) 4.8 (d,1, J=4), 6.7-7.3 (m,5), 7.5-8.0 (m,5). Analysis for C31H34Cl2N2O3S.HCl.1.5 H2O: Calculated: C, 59.86; H, 5.67, N, 4.50; Found: C, 57.05; H, 5.64; N, 4.19.

Workup

  1. customThe reaction product was purified by chromatography

Sources & evidence

ORD record
ord-7c18495e61cb4d6c881a4841625be57f
Source dataset
uspto-grants-1996_12
Patent number
US05589489

Reaction notes

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