Trifluoroacetic acid → 2-(Piperazine-1-carbonyl)-benzoic acid methyl ester

HRID 1178123Notes

Reaction equation

HRID 1178123 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([O:30][CH3:31])=[O:29])[CH2:17][CH2:16]1)=O)(C)(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:31][O:30][C:28](=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]([N:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1)=[O:32]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 59559652tert-Butyl 4-{[2-(methoxycarbonyl)phenyl]carbonyl}piperazine-1-carboxylate

Product 1

HCID 595596032-(Piperazine-1-carbonyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1.2 mL) was added to a stirred solution of 4-(2-Methoxycarbonyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester (200 mg, 0.58 mmol) in DCM (5 mL) at 0° C. The resulting mixture was stirred at the same temperature for 2 hours. DIPEA (1.5 mL) was added to the cold reaction mixture and the mixture was concentrated under reduced pressure to afford 2-(piperazine-1-carbonyl)-benzoic acid methyl ester.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dcb5c2e17e6c4061953d601bec78ae00
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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