Methanol → HCID 67713289, compound

HRID 2256052Notes

Reaction equation

HRID 2256052 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)=[O:3].[Cl:16][C:17]1[CH:18]=[C:19]([C@H:24]([CH2:36][CH:37]=O)[CH2:25][N:26]([CH3:35])[C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:20]=[CH:21][C:22]=1[Cl:23].ClCCl.CO>O>[ClH:16].[Cl:16][C:17]1[CH:18]=[C:19]([C@H:24]([CH2:36][CH2:37][N:13]2[CH2:14][CH2:15][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([S:2]([CH3:1])=[O:3])=[CH:9][CH:8]=3)[CH2:11][CH2:12]2)[CH2:25][N:26]([CH3:35])[C:27](=[O:34])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:20]=[CH:21][C:22]=1[Cl:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 15381108(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamideHCID 226224724-[4-(Methanesulfinyl)phenyl]piperidine

Product 1

HCID 67713289HCID 67713289, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using a procedure similar to that described in Example 1 (alternative preparation), except using 4-(4-methylsulfinylphenyl)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 94°-125° C.; MS: 557; NMR (CD3OD): 1.8-2.3 (m, 6), 2.8 (s, 6), 2.8-3.3 (br, 6), 3.4-3.9 (m, 4), 7.9-7.7 (m, 12). Analysis for C30H34Cl2NO2S·1.0 HCl·1.5 H2O: Calculated: C, 58.02; H, 6.17; N, 4.51; Found: C, 57.74; H, 6.00; N, 5.01.

Workup

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

Sources & evidence

ORD record
ord-f22a72c49c53456986d23c2d6d910b8b
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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