Citric Acid → 4'-Trifluoromethyl-biphenyl-2-carboxylic acid [4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenyl]-amide citrate salt

HRID 1267139Notes

Reaction equation

HRID 1267139 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:38]=[CH:39][CH:40]=1)[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[C:23]([C:28]4[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=4)=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:21])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)#[N:2].[C:41]([OH:53])(=[O:52])[CH2:42][C:43]([CH2:48][C:49]([OH:51])=[O:50])([C:45]([OH:47])=[O:46])[OH:44]>CO>[C:41]([OH:53])(=[O:52])[CH2:42][C:43]([CH2:48][C:49]([OH:51])=[O:50])([C:45]([OH:47])=[O:46])[OH:44].[C:1]([C:3]1[CH:4]=[C:5]([CH:38]=[CH:39][CH:40]=1)[CH2:6][N:7]1[CH2:8][CH2:9][N:10]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20]([C:22]3[C:23]([C:28]4[CH:33]=[CH:32][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:30][CH:29]=4)=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:21])=[CH:17][CH:18]=2)[CH2:11][CH2:12]1)#[N:2]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 98073154'-Trifluoromehtyl-biphenyl-2-carboxylic acid [4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenyl]-amide

Product 1

HCID 865913074'-Trifluoromethyl-biphenyl-2-carboxylic acid [4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenyl]-amide citrate saltYield 55.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4′-trifluoromethyl-biphenyl-2-carboxylic acid [4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenyl]-amide (0.2 g) in MeOH (15 mL) was added citric acid (71 mg) and the resulting solution was stirred at room temperature. The solution was then evaporated to dryness and the solid was triturated in Et2O, filtered and dried to give the title compound (0.15 g) as a white powder.

Workup

  1. customThe solution was then evaporated to dryness
  2. customthe solid was triturated in Et2O
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-12bee99cee404722b5daf00838a8d544
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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