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

HRID 1664120Notes

Reaction equation

HRID 1664120 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.BrC1C=CC(F)=CC=1C(O)=O.[C:32]([C:36]([OH:38])=[O:37])([F:35])([F:34])[F:33]>C(Cl)Cl>[F:33][C:32]([F:35])([F:34])[C:36]([OH:38])=[O:37].[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

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 27781812-Bromo-5-fluorobenzoic 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-7e98c8eae9884b3f8eef1cb5c6c51529
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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