4-(2-(Methylsulfinyl)phenyl)piperidine → (3R)-3-[(1S)-1-(3,4-Dichlorophenyl)-3-(4-(2-methylsulfinylphenyl)piperidino)propyl]-2-ethyl-2,3-dihydro-isoindol-1-one hydrochloride

HRID 725116Notes

Reaction equation

HRID 725116 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([C@@H: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:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)=[O:27]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([C@@H: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:37]2[CH2:38][CH2:39][CH:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[S:26]([CH3:25])=[O:27])[CH2:35][CH2:36]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 187003874-(2-(Methylsulfinyl)phenyl)piperidineHCID 57119143(3S)-3-(3,4-Dichlorophenyl)-3-[(1R)-2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl]propionaldehyde

Product 1

HCID 70110105(3R)-3-[(1S)-1-(3,4-Dichlorophenyl)-3-(4-(2-methylsulfinylphenyl)piperidino)propyl]-2-ethyl-2,3-dihydro-isoindol-1-one hydrochlorideYield 74.7%

Procedure

(3S)-3-(3,4-Dichlorophenyl)-3-[(1R)-2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl]propionaldehyde (0.4 g) was coupled to 4-(2-methylsulfinylphenyl)piperidine (0.36 g) using a method similar to that described in Example 1, to afford the title compound (0.25 g); mp 120°-125° C. (d); MS: m/z=569(M+1); NMR (CDCl3): 1.20 (m,3), 2.69 (s,3), 4.88 (m,1), 6.59-7.9 (m,11). Analysis for C31 H34Cl2N2O2S.HCl.1.5 H2O: Calculated: C, 58.82; H, 6.05, N, 4.43; Found: C, 58.51; H, 6.07; N, 4.59.

Sources & evidence

ORD record
ord-121a8ea8316242fab12876ecf15416b1
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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