1-(m-Tolyl)piperazine → {(2s,4s)-1-Benzyl-4-[(3,5-bis-trifluoromethyl-benzyl)-methyl-amino]-pyrrolidin-2-yl}-(4-m-tolyl-piperazin-1-yl)-methanone

HRID 490633Notes

Reaction equation

HRID 490633 reaction equation
CO[C:3]([CH:5]1[CH2:9][C:8](=O)[CH2:7][N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].[F:18][C:19]([F:34])([F:33])[C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:23][NH:24][CH3:25].[C:35]1([CH3:47])[CH:40]=[CH:39][CH:38]=[C:37]([N:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)[CH:36]=1>>[CH2:11]([N:6]1[CH2:7][C@@H:8]([N:24]([CH2:23][C:22]2[CH:21]=[C:20]([C:19]([F:33])([F:34])[F:18])[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=2)[CH3:25])[CH2:9][C@H:5]1[C:3]([N:44]1[CH2:45][CH2:46][N:41]([C:37]2[CH:36]=[C:35]([CH3:47])[CH:40]=[CH:39][CH:38]=2)[CH2:42][CH2:43]1)=[O:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 831111-(m-Tolyl)piperazineHCID 10956204{[3,5-Bis(trifluoromethyl)phenyl]methyl}(methyl)amineHCID 67548133Benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 87440579{(2s,4s)-1-Benzyl-4-[(3,5-bis-trifluoromethyl-benzyl)-methyl-amino]-pyrrolidin-2-yl}-(4-m-tolyl-piperazin-1-yl)-methanoneYield 13.4%

Procedure

As described for Example 56b and 56d, 1-benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester (100 mg, 0.428 mmol) was converted, using (3,5-bis-trifluoromethyl-benzyl)-methyl-amine instead of 3,5-bis-trifluoromethyl-benzylamine, and using 1-m-tolyl-piperzine instead of 1-(3-trifluoromethyl-phenyl)-piperazine, to the title compound (12.1 mg, 13.4%) as light yellow oil. MS m/e=619.4[M+H]+.

Sources & evidence

ORD record
ord-f58dc481110c4d759a0811e5e0784d07
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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