Trifluoroacetic acid → 5-Chloro-2-(piperazin-1-yl)benzonitrile

HRID 557031

Reaction equation

HRID 557031 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[C:21]#[N:22])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[C:15]([CH:16]=1)[C:21]#[N:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667578634-(4-Chloro-2-cyano-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 193671275-Chloro-2-(piperazin-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-chloro-2-cyano-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.32 g, 1 mmol) in dichloromethane cooled at 0° C. was treated with trifluoroacetic acid (20%) and warmed to room temperature and stirred for 2 h. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and free based with 10% aqueous sodium bicarbonate. The organic layers were separated and dried over sodium sulfate and concentrated in vacuo. The product used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. customThe organic layers were separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe product used without further purification

Sources & evidence

ORD record
ord-15d475cc9307404a9bf3109fd7d26853
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Linked notes

Loading…