Methanol → HCID 67713107, compound

HRID 2256051Notes

Reaction equation

HRID 2256051 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[Cl:15][C:16]1[CH:17]=[C:18]([C@H:23]([CH2:35][CH:36]=O)[CH2:24][N:25]([CH3:34])[C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:19]=[CH:20][C:21]=1[Cl:22].ClCCl.CO>O>[ClH:15].[Cl:15][C:16]1[CH:17]=[C:18]([C@H:23]([CH2:35][CH2:36][N:12]2[CH2:13][CH2:14][CH:9]([C:6]3[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=3)[CH2:10][CH2:11]2)[CH2:24][N:25]([CH3:34])[C:26](=[O:33])[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:19]=[CH:20][C:21]=1[Cl:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 15381108(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamideHCID 497608044-[4-(Methylsulfanyl)phenyl]piperidine

Product 1

HCID 67713107HCID 67713107, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using a procedure similar to that described in Example 1 (alternative preparation), except using 4-(4-methylthiophenyl)piperidine and (S)-N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methylbenzamide, the title compound was prepared. Chromatography with dichloromethane:methanol followed by conversion to the hydrochloride salt gave a white solid; mp 73-92(dec) °C.; MS: 541; NMR (CD3OD): 1.8-2.2 (m, 6), 2.4 (s, 1), 2.7 (s, 3), 2.6-3.2 (m, 6), 3.4-3.8 (m, 4), 6.9 (d, J=7, 1), 7.1-7.2 (m, 6), 7.3 (m, 5), 7.5(m, 1). Analysis for C30H34Cl2NO2S·1.0HCl·1.0 H2O: Calculated: C, 60.45; H, 6.26; N, 4.70; Found: C, 60.23; H, 5.85; N, 4.70.

Workup

  1. customthat described in Example 1 (alternative preparation)
  2. customgave a white solid

Sources & evidence

ORD record
ord-f9e8d7e773c54526b6edeabfa4f20707
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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