Trifluoroacetic acid → 1-[2-(Trifluoromethyl)benzoyl]piperazine

HRID 655602Notes

Reaction equation

HRID 655602 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:25])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:23])[F:22])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:11]1([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:23])([F:22])[F:24])=[O:25])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44203151HCID 44203151, compound

Product 1

HCID 167337841-[2-(Trifluoromethyl)benzoyl]piperazineYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-trifluoromethylbenzoyl)piperazine-1-carboxylic acid tert-butyl ester (10 mmol) in 50 mL of 1:4 mixture of trifluoroacetic acid and dichloromethane was stirred at ambient temperature for 10 minutes. After concentration in vacuo the residue was dissolved in dichloromethane (100 mL) and washed sequentially with 1 N NaOH (10 mL), H2O, brine, and then dried over MgSO4, filtered and concentrated in vacuo to yield piperazin-1-yl-(2-trifluoromethylphenyl)methanone as light yellow oil. Yield 91%, 2.350 g.

Workup

  1. concentrationAfter concentration in vacuo the residue
  2. dissolutionwas dissolved in dichloromethane (100 mL)
  3. washwashed sequentially with 1 N NaOH (10 mL), H2O, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e05a68bfbeb4aa9827457f5672d3d67
Source dataset
uspto-grants-2011_12
Patent number
US08071603B2

Reaction notes

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