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

HRID 490635Notes

Reaction equation

HRID 490635 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[CH2:10][CH:9]1[C:29]([OH:31])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]1([CH3:44])[CH:37]=[CH:36][CH:35]=[C:34]([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH:33]=1>>[CH2:1]([N:8]1[CH2:12][C@@H:11]([NH:13][CH2:14][C:15]2[CH:16]=[C:17]([C:25]([F:28])([F:26])[F:27])[CH:18]=[C:19]([C:21]([F:22])([F:24])[F:23])[CH:20]=2)[CH2:10][C@H:9]1[C:29]([N:41]1[CH2:42][CH2:43][N:38]([C:34]2[CH:33]=[C:32]([CH3:44])[CH:37]=[CH:36][CH:35]=2)[CH2:39][CH2:40]1)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 831111-(m-Tolyl)piperazineHCID 866253011-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid

Product 1

HCID 87440142[(2s,4s)-1-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidin-2-yl]-(4-m-tolyl-piperazin-1-yl)-methanoneYield 8.5%

Procedure

As described for Example 56d, 1-benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid (65 mg, 0.146 mmol) was converted, using 1-m-tolyl-piperzine instead of 1-(3-trifluoromethyl-phenyl)-piperazine, to the title compound (7.5 mg, 8.5%) as light yellow oil. MS m/e=605.4 [M+H]+.

Sources & evidence

ORD record
ord-d2d32b50641540d4be6fa03fbb04c6bd
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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