N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide → (S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(3-methyl-2-thioxoperhydropyrimidin-1-yl)piperidino]butyl]-N-methylbenzamide hydrochloride

HRID 343471Notes

Reaction equation

HRID 343471 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[C:3]1=[S:14].[Cl:15][C:16]1[CH:17]=[C:18]([CH: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]>>[ClH:15].[Cl:15][C:16]1[CH:17]=[C:18]([C@H:23]([CH2:35][CH2:36][N:11]2[CH2:12][CH2:13][CH:8]([N:4]3[CH2:5][CH2:6][CH2:7][N:2]([CH3:1])[C:3]3=[S:14])[CH2:9][CH2:10]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

3

Reactant 2

HCID 22137499N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamideHCID 221375094-(3-Methyl-2-thioxoperhydropyrimidin-1-yl)piperidine

Product 1

HCID 86589869(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(3-methyl-2-thioxoperhydropyrimidin-1-yl)piperidino]butyl]-N-methylbenzamide hydrochloride

Procedure

Using the procedure of Example 1, replacing 4-(2-oxo-1,3-oxazolidin-3-yl)piperidine with 4-(3-methyl-2-thioxoperhydropyrimidin-1-yl)-piperidine, and N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methylbenzamide with the (S)-enantiomer, the title compound was obtained as a white solid; MS: m/z=547(M+1); Analysis for C28H36Cl2N4OS.1.70 HCl.0.10 (C2H5)2O: Calculated: C, 55.28; H, 6.32; N, 9.08; Found: C, 55.21; H, 6.37; N, 8.88.

Sources & evidence

ORD record
ord-c71586b5f0de49c0ad3e1da9aa735b4d
Source dataset
uspto-grants-1999_01
Patent number
US05861392

Reaction notes

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