4-[2-(Methylsulfanyl)phenyl]piperidine → 3-[1-(3,4-Dichlorophenyl)-3-(4-(2-methylthiophenyl)piperidino)propyl]-2-ethyl-2,3-dihydroisoindol-1-one hydrochloride

HRID 725113Notes

Reaction equation

HRID 725113 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:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1>>[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:36]2[CH2:37][CH2:38][CH:33]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[S:26][CH3:25])[CH2:34][CH2:35]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 190291654-[2-(Methylsulfanyl)phenyl]piperidineHCID 218397513-(3,4-dichlorophenyl)-3-(2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde

Product 1

HCID 218398453-[1-(3,4-Dichlorophenyl)-3-(4-(2-methylthiophenyl)piperidino)propyl]-2-ethyl-2,3-dihydroisoindol-1-one hydrochlorideYield 106.8%

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-methylthiophenyl)piperidine (0.414 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 (0.63 g); mp 110°-140° C. (d); MS: m/z=553(M+1); NMR (CDCl3): 1.19 (m,3), 2.0 (m,2), 2.45 (s,3), 2.68 (m,7), 3.16 (m,3), 3.56 (m,4), 4.18 (m,1), 4.86 (d,1, J=3.7), 6.56-7.79 (m,11). Analysis for C31H34Cl2N2OS.HCl: Calculated: C, 63.1; H, 5.97, N, 4.75; Found: C, 62.94; H, 5.94; N, 4.82.

Workup

  1. customThe reaction product was not purified by chromatography

Sources & evidence

ORD record
ord-709b3eba866b4027a236a8d94cdae95a
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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