1-(2-Fluorophenyl)piperazine → {(2S,4S)-1-Benzyl-4-[(3,5-bis-trifluoromethyl-benzyl)-methyl-amino]-pyrrolidin-2-yl}-[4-(2-fluoro-phenyl)-piperazin-1-yl]-methanone

HRID 490637Notes

Reaction equation

HRID 490637 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].[F:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]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:45]1[CH2:44][CH2:43][N:42]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[F:35])[CH2:47][CH2:46]1)=[O:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 705291-(2-Fluorophenyl)piperazineHCID 10956204{[3,5-Bis(trifluoromethyl)phenyl]methyl}(methyl)amineHCID 67548133Benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 86625306{(2S,4S)-1-Benzyl-4-[(3,5-bis-trifluoromethyl-benzyl)-methyl-amino]-pyrrolidin-2-yl}-[4-(2-fluoro-phenyl)-piperazin-1-yl]-methanoneYield 6%

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-(2-fluoro-phenyl)-piperazine instead of 1-(3-trifluoromethyl-phenyl)-piperazine, to the title compound (5.5 mg, 6.0%) as light yellow oil. MS m/e=623.4 [M+H]+.

Sources & evidence

ORD record
ord-ab2de686c11b4a4bae5a9e89b1bd241a
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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