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

HRID 557029Notes

Reaction equation

HRID 557029 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 The product
  6. customwas used without further purification ESI-MS m/z

Sources & evidence

ORD record
ord-a8c8ffc28c824db3b031e00b9c481a7e
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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