Carbamate → Benzenemethanamine, N-methyl-4-(trifluoromethyl)-

Participants

Reaction Steps

A mixture of 4-(trifluoromethyl)benzylamine (1.0 mL, 7.02 mmol) and di-tert-butyl carbonate (1.68 g, 7.72 mmol) in CH2Cl2 (10 mL) was stirred for 1 hour. The reaction mixture was poured into saturated aqueous ammonium chloride solution, extracted with CH2Cl2 and the organic layers were combined, dried over MgSO4 and concentrated in vacuo to give a white crystalline solid. To a solution of the crude carbamate (1.00 g, 3.61 mmol) in THF (20 mL) in a room temperature water bath, was added LiAlH4 (0.69 g, 18.1 mmol) portion-wise over 10 minutes. The reaction was then heated at reflux for 4 hours. The reaction was cooled in ice and quenched by the addition of water (1.6 mL) and NaOH (2N, 1.3 mL). The grey slurry was filtered and washed with MeOH. The MeOH was removed in vacuo and the crude product taken up in CH2Cl2 and dried over MgSO4 and concentrated in vacuo. Purification by flash column chromatography eluting with 5-10% MeOH in CH2Cl2 plus 1% NH3 solution (2N in MeOH) afforded the title compound.

Provenance & Evidence