Trifluoroacetic acid → 1-[2-Chloro-4-(trifluoromethyl)phenyl]piperazine

HRID 32651Notes

Reaction equation

HRID 32651 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[Cl:24])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:24][C:15]1[CH:16]=[C:17]([C:20]([F:21])([F:22])[F:23])[CH:18]=[CH:19][C:14]=1[N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 534855184-(2-Chloro-4-trifluoromethylphenyl)piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 468374961-[2-Chloro-4-(trifluoromethyl)phenyl]piperazineYield 46.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4-(2-Chloro-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (60 mg, 0.164 mmol) in MeCl2 (0.8 ml) was treated with trifluoroacetic acid (63 μl), heated up to 40° C. and stirred for 4 h. The solvent was removed in vacuo. The residue was dissolved in water and basified with NaOH 1N. The aqueous layer was extracted twice with MeCl2. The combined organic layers were dried over Na2SO4, filtered and the solvent was removed in vacuo to provide the title compound (20 mg, 46%) as a yellow oil, MS (m/e): 265.0 (MH+, 100%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water and basified with NaOH 1N
  3. extractionThe aqueous layer was extracted twice with MeCl2
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-39581405aed64fa5831a618fb56b7429
Source dataset
uspto-grants-2008_09
Patent number
US07427612B2

Reaction notes

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