Methanol → HCID 9873305, compound

HRID 2256049Notes

Reaction equation

HRID 2256049 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]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:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[S:2]([CH3:1])=[O: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 187003874-(2-(Methylsulfinyl)phenyl)piperidine

Product 1

HCID 9873305HCID 9873305, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using a procedure similar to that described in Example 1 (alternative preparation), except using 4-(2-methylsulfinylphenyl)piperidine and (S)-N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methyl-benzamide, the title compound was prepared. Chromatography with dichloromethane:methanol followed by conversion to the hydrochloride salt gave a white solid; mp 71°-144° C.; MS: 557; NMR (CD3OD): 1.9-2.3 (m, 6), 2.4 (s, 1), 2.7-2.8 (two s, 3), 2.9-3.4 (br, 6), 3.5-3.9 (m, 4), 7.0 (m, 4), 7.3-7.6 (m, 7), 7.5-7.6 (m, 2). Analysis for C30H34Cl2NO2S·1.0 HCl·1.0 H2O: Calculated: C, 60.45; H, 6.26; N, 4.70; Found: C, 60.43; H, 5.91; N, 4.63.

Workup

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

Sources & evidence

ORD record
ord-13a6e04d188847ffb15101e94526600b
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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