Trifluoroacetic acid → 2-(Aminomethyl)-5-fluoro-n-methylbenzamide trifluoroacetate salt

HRID 348120Notes

Reaction equation

HRID 348120 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7]C(=O)OC(C)(C)C)=[C:4]([C:17](=[O:20])[NH:18][CH3:19])[CH:3]=1.[C:21]([C:25]([OH:27])=[O:26])([F:24])([F:23])[F:22]>C(Cl)Cl>[F:22][C:21]([F:24])([F:23])[C:25]([OH:27])=[O:26].[NH2:7][CH2:6][C:5]1[CH:15]=[CH:16][C:2]([F:1])=[CH:3][C:4]=1[C:17]([NH:18][CH3:19])=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11984298Tert-butyl 4-fluoro-2-[(methylamino)carbonyl]benzylcarbamate

Product 1

HCID 210698142-(Aminomethyl)-5-fluoro-n-methylbenzamide trifluoroacetate saltYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-fluoro-2-(methylcarbamoyl)benzylcarbamate (7.70 g, 27.3 mmol; prepared from 2-bromo-5-fluorobenzoic acid using literature methods) in CH2Cl2 (100 mL) was added CF3CO2H (25 mL) and the mixture stirred at room temperature for 15 min. This was concentrated in vacuo and the residue triturated with diethyl ether to obtain 8.0 g (Yield 99%) of the title compound as a white powder. 1H NMR (300 MHz, D2O) δ ppm: 2.93 (3H, s) 4.20 (2H, s) 7.35 (1H, dt, J=8.5, 3 Hz) 7.42 (1H, dd, J=9.0, 2.7 Hz) 7.57 (1H, dd, J=8.4, 5.5 Hz); LC/MS m/z 183 (M+H).

Workup

  1. concentrationThis was concentrated in vacuo
  2. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-00bd981a0c2447ff9afadabca3988d5e
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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