Hydrochloric Acid → 4,4,4-trifluoro-2-methylbutan-1-amine hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a suspension of lithium aluminum hydride (15.5 g) in diethyl ether (290 ml) was added a solution of 2-methyl-4,4,4-trifluorobutyramide (31.74 g) in diethyl ether (0.5 L) at a rate to obtain a gentle reflux. After heating at reflux for 12 hours and cooling to 0° C., the reaction was quenched with saturated sodium sulfate solution and allowed to warm to ambient temperature. The mixture was dried (Na2SO4) and filtered through diatomaceous earth with diethyl ether wash. The filtrate was treated with gaseous hydrochloric acid (14.9 g, 0.409 mol) and then the solvent was evaporated. The residue was dissolved in methylene chloride and combined with product from a similar reaction of 2-methyl-4,4,4-trifluorobutyramide (25 g). Recrystallization from methylene chloride and diethyl ether, followed by trituration with ethyl acetate, afforded 2-methyl-4,4,4-trifluorobutylamine hydrochloride (51.35 g, 79%) as a light pink solid; mp 224.5°-225.5° C.; MS(CI): 142 (M+H-HCl). Analysis for C5H11ClF3N: Calculated: C, 33.81; H, 6.24; N, 7.89. Found: C, 33.93; H, 6.13; N, 8.17.

Provenance & Evidence