Trifluoroacetic acid → 4'-Trifluoromethyl-biphenyl-2-carboxylic acid [4-(piperazinyl)-phenyl]-amide

HRID 1267115Notes

Reaction equation

HRID 1267115 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[C:24]([C:29]4[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=4)=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N:11]1([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([C:23]3[C:24]([C:29]4[CH:34]=[CH:33][C:32]([C:35]([F:37])([F:36])[F:38])=[CH:31][CH:30]=4)=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:22])=[CH:18][CH:19]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54191977HCID 54191977, compound

Product 1

HCID 112010994'-Trifluoromethyl-biphenyl-2-carboxylic acid [4-(piperazinyl)-phenyl]-amideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{4-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino)-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (11.7 g) in CH2Cl2 (50 mL) was added trifluoroacetic acid (25 mL) and the solution was stirred at room temperature for 2 hours. The mixture was then evaporated under reduced pressure and the residue was taken in water. The resulting precipitate was filtered and washed with water. The resulting solid was then suspended in water, basified with a saturated solution of Na2CO3, and extracted with CH2Cl2. The organic phase was then washed with water, dried over Na2SO4, filtered and evaporated to give the title compound (9 g) as white crystals.

Workup

  1. customThe mixture was then evaporated under reduced pressure
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. extractionextracted with CH2Cl2
  5. washThe organic phase was then washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-c9e75fa80c334865967f0c2b80327bc1
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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