Trifluoroacetic acid → 1-(4-Chloro-o-tolyl)piperazine

HRID 1983745Notes

Reaction equation

HRID 1983745 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[CH3:21])[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[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[C:15]([CH3:21])[CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66757902Tert-butyl 4-(4-chloro-2-methylphenyl)piperazine-1-carboxylate

Product 1

HCID 1008521-(4-Chloro-o-tolyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-chloro-2-methyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.26 g, 0.837 mmol) in dichloromethane cooled at 0° C. was treated with trifluoroacetic acid (20%) and warmed to room temperature and stirred for 2 hours. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and free based with 10% aqueous sodium bicarbonate. The organics were separated and dried over sodium sulfate and concentrated. The product was used without further purification ESI-MS m/z: 211 (M+1), UV retention time: 1.25 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. customThe organics were separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product was used without further purification ESI-MS m/z

Sources & evidence

ORD record
ord-5c2edd0c58f24f7dbbd114ebaabfc92e
Source dataset
uspto-grants-2009_06
Patent number
US07541365B2

Reaction notes

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