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

HRID 2356590Notes

Reaction equation

HRID 2356590 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-4461ff68b5bb4ccbb9b78fa6bf65d3a9
Source dataset
uspto-grants-2010_07
Patent number
US07759348B2

Reaction notes

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