Trifluoroacetic acid → 2-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone

HRID 1177868Notes

Reaction equation

HRID 1177868 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][CH2:15][C:16](=[O:35])[N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[CH2:19][CH2:18]1)(C)(C)C>C(Cl)Cl>[NH2:14][CH2:15][C:16]([N:17]1[CH2:18][CH2:19][N:20]([C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:31])[F:32])[CH2:21][CH2:22]1)=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 59559599{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 595596292-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanoneYield 126.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (13 mL) was added drop wise to {2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester (2.6 g, 6.27 mmol) in DCM (15 mL) at 0° C. The resulting mixture was stirred at room temperature for 2 hours. Concentrating the mixture afforded a crude product, which was recrystallized from hexane to afford 2.5 g (93% yield) of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone as TFA salt.

Workup

  1. concentrationConcentrating the mixture
  2. customafforded a crude product, which
  3. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-bb02afe912cf494093109cd497dfdd1a
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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