Trifluoroacetic acid → 1-(2-Phenylethyl)piperazin-2-one

HRID 609647Notes

Reaction equation

HRID 609647 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]([C:19](=[O:22])[CH2:20]Br)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:13]1([CH2:12][CH2:11][N:10]2[CH2:9][CH2:8][NH:7][CH2:20][C:19]2=[O:22])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 107863102-[(Bromoacetyl)(2-phenylethyl)amino]ethyl carbamic acid tert-butyl ester

Product 1

HCID 105361961-(2-Phenylethyl)piperazin-2-oneYield 256.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(bromoacetyl)(2-phenylethyl)amino]ethyl carbamic acid tert-butyl ester (0.81 g, 2.1 mmol) in CH2Cl2 (25 mL) was added trifluoroacetic acid (2.5 mL) and the mixture stirred for 1 h. The solvent was removed in vacuo and the residue azeotroped with toluene (10 mL) and CH2Cl2 (2×10 mL). The crude amine (1.1 g) was isolated as its trifluoroacetate salt, as a pale yellow oil and used crude in the subsequent reaction.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped with toluene (10 mL) and CH2Cl2 (2×10 mL)

Sources & evidence

ORD record
ord-687b3ce2e5e6431d9eab1daf0c687cc2
Source dataset
uspto-grants-1999_12
Patent number
US05998415

Reaction notes

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