Trifluoroacetic acid → Methyl 5-Chloro-2-(1-piperazinyl)benzoate

HRID 917182Notes

Reaction equation

HRID 917182 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]([O:23][CH3:24])=[O:22])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:24][O:23][C:21](=[O:22])[C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667586124-(4-Chloro-2-methoxycarbonyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66757938Methyl 5-Chloro-2-(1-piperazinyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-chloro-2-methoxycarbonyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.32 g, 0.92 mmol) in dichloromethane (5.0 mL) 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 organics were separated and dried over sodium sulfate and concentrated in vacuo. The product used without any further purification. ESI-MS m/z: 255 (M+1), UV retention time: 1.14 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 in vacuo
  6. customThe product used without any further purification

Sources & evidence

ORD record
ord-5eb064c073b545049e8add0d4d0fdd9f
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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