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

HRID 917176Notes

Reaction equation

HRID 917176 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-2b8b5a402f54406bb7523ac05620fb54
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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