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

HRID 2354824
Notes
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Reaction equation

HRID 2354824 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-b028bed0e93343298c4aa4653b18ef51
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07754711B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes