Trifluoroacetic acid → (4-Amino-3-chlorophenyl)(piperazin-1-yl)methanone

HRID 1807730Notes

Reaction equation

HRID 1807730 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]=1[Cl:23].FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[O:7])=[CH:4][C:3]=1[Cl:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67059646HCID 67059646, compound

Product 1

HCID 64322197(4-Amino-3-chlorophenyl)(piperazin-1-yl)methanoneYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 4-(4-amino-3-chlorobenzoyl)piperazine-1-carboxylate (45.3 mmol, 15.4 g), dichloromethane (50 mL) and 2,2,2-trifluoroacetic acid (136 mmol, 15.50 g) were stirred for 24 hours. The reaction was concentrated under reduced pressure and was then basified with potassium carbonate (aqueous). The aqueous was extracted with ethyl acetate and then dichloromethane to give the title compound (7.7 g).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. extractionThe aqueous was extracted with ethyl acetate

Sources & evidence

ORD record
ord-b6424aa08085429f94782db21b990603
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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