Diisopropylethylamine → Ethanamine, N-methyl-2-[3-(trifluoromethyl)phenoxy]-

Participants

Reaction Steps

A mixture of methylamine hydrochloride salt (380 mg, 5.57 mmol) in tetrahydrofuran (10 mL) was treated with N,N-diisopropylethylamine (1.44 g, 11.15 mmol) and 3-(2-bromoethoxy)benzotrifluoride (300 mg, 1.11 mmol). The reaction mixture was allowed to stir at reflux for 2 d. At this time, the reaction was quenched by the addition of water. The aqueous layer was extracted with ethyl acetate. The organics were washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 methylene chloride/methanol) afforded methyl-[2-(3-trifluoromethyl-phenoxy)-ethyl]-amine (110 mg, 45%) as yellow solid. The NMR spectrum obtained on the sample is compatible with its structure.

Provenance & Evidence