Trifluoroacetic acid → N-tert-butyl-2-fluoro-3-(piperazin-1-ylmethyl)benzamide

HRID 1878408Notes

Reaction equation

HRID 1878408 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:9]([F:28])=[C:10]([CH:25]=[CH:26][CH:27]=1)[CH2:11][N:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([NH:5][C:6](=[O:7])[C:8]1[CH:27]=[CH:26][CH:25]=[C:10]([CH2:11][N:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)[C:9]=1[F:28])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57917710tert-Butyl 4-(3-(tert-butylcarbamoyl)-2-fluorobenzyl)piperazine-1-carboxylate

Product 1

HCID 57917605N-tert-butyl-2-fluoro-3-(piperazin-1-ylmethyl)benzamideYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of tert-butyl 4-(3-(tert-butylcarbamoyl)-2-fluorobenzyl)piperazine-1-carboxylate (2.54 mmol, 1 g) in dichloromethane at room temperature was added trifluoro-acetic acid (53.9 mmol, 4 mL, 6.14 g). After 3 hours stirring the reaction was concentrated under reduced pressure. The residue was taken up in dichloromethane/methanol and loaded on to strong cation exchange column (10 g) and washed with dichloromethane/methanol. Elution of the column with 2M ammonia in methanol gave the title compound (636 mg). MS (ESI) m/z 294.4 [M+H]+

Workup

  1. concentrationwas concentrated under reduced pressure
  2. washwashed with dichloromethane/methanol
  3. washElution of the column with 2M ammonia in methanol

Sources & evidence

ORD record
ord-26bcf293ffd146baa212db40ae983915
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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