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

HRID 389972Notes

Reaction equation

HRID 389972 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 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-trifluoromethylbenzoyl)piperazine-1-carboxylic acid tert-butyl ester (0.948 g, 2.65 mmol) in 50 mL of a 1:4 mixture of trifluoroacetic acid and dichloromethane was stirred at room temperature for 20 h. After concentration in vacuo, the residue was dissolved in dichloromethane (100 mL) and washed with 1 N NaOH (10 mL), water (15 mL), and brine (15 mL). The organic phase was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to yield the title compound as a light brown oil (0.657 g, 2.54 mmol). 1H NMR (300 MHz, CDCl3) δ 7.69, 7.54, 7.30, 3.78, 3.15, 2.94, 2.76. MS (ES+) m/z 259.3 (M+1).

Workup

  1. concentrationAfter concentration in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane (100 mL)
  3. washwashed with 1 N NaOH (10 mL), water (15 mL), and brine (15 mL)
  4. dry with materialThe organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-42cda02926164e0a8e9ed256ab73716d
Source dataset
uspto-grants-2013_02
Patent number
US08383628B2

Reaction notes

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