3-(Piperidin-4-yl)pyridine → (S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(3-pyridyl)piperidino]butyl]-N-methylbenzamide hydrochloride

HRID 2256038Notes

Reaction equation

HRID 2256038 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:2]=1.[Cl:13][C:14]1[CH:15]=[C:16]([C@H:21]([CH2:33][CH:34]=O)[CH2:22][N:23]([CH3:32])[C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:17]=[CH:18][C:19]=1[Cl:20]>ClCCl.CO>[ClH:13].[Cl:13][C:14]1[CH:15]=[C:16]([C@H:21]([CH2:33][CH2:34][N:10]2[CH2:11][CH2:12][CH:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH2:8][CH2:9]2)[CH2:22][N:23]([CH3:32])[C:24](=[O:31])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

4

Reactant 2

HCID 46903903-(Piperidin-4-yl)pyridineHCID 15381108(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide

Product 1

HCID 67713066(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(3-pyridyl)piperidino]butyl]-N-methylbenzamide hydrochloride

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Using a procedure similar to that described in Example 1 (alternative procedure), 4-(3-pyridyl)piperidine was alkylated using (S)-N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methylbenzamide. Chromatography of the crude product, with dichloromethane:methanol (9:1) as the eluent, followed by conversion to the hydrochloride salt gave the title compound as a white solid (0.253 g); mp 70°-140° C. (dec); NMR: 1.8-2.4 (m, 6), 2.73 (s, 3), 2.8-3.2 (broad s, 5), 7.0-7.2 (m, 3), 7.4 (s, 4), 7.5-7.7 (m, 2), 7.9 (m, 1), 8.2 (broad s, 1), 8.7 (d, 2 J=5); MS: m/z=496(M+1). Analysis for C28H31ClN3O·2.2 HCl·3 H2O: Calculated: C, 53.94; H, 6.31; N, 6.74; Found: C, 53.53; H, 6.16; N, 6.65.

Sources & evidence

ORD record
ord-b58afe6c26834a1896d8c1b93dfe55d2
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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