4-(2-Trifluoromethylthiobenzoyl)piperazine-1-carboxylic acid tert-butyl ester → Methanethione, 1-piperazinyl[2-(trifluoromethyl)phenyl]-

HRID 2056612Notes

Reaction equation

HRID 2056612 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[S: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>ClCCl.FC(F)(F)C(O)=O>[N:11]1([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:22])[F:23])=[S:25])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 865972314-(2-Trifluoromethylthiobenzoyl)piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86025958Methanethione, 1-piperazinyl[2-(trifluoromethyl)phenyl]-Yield 95.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(2-trifluoromethylthiobenzoyl)piperazine-1-carboxylic acid tert-butyl ester (2.1 g, 5.61 mmol) in dichloromethane and trifluoroacetic acid (30 mL, 2:1) was stirred at ambient temperature overnight, the solvents were removed by evaporation. The residue was dissolved in ethyl acetate, and washed with aqueous saturated NaHCO3 and brine, dried over anhydrous Na2SO4 and concentrated to give piperazin-1-yl-(2-trifluoromethylphenyl)methanethione (1.47 g, 5.36 mmol) which was used directly for next step without further purification.

Workup

  1. customthe solvents were removed by evaporation
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with aqueous saturated NaHCO3 and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a68bfd3afed34c5fa64199572422a599
Source dataset
uspto-grants-2008_02
Patent number
US07335658B2

Reaction notes

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