NN-dimethyl-2-fluoro-2-phenylethylamine: preparation and solvolysis in aqueous acetone

Abstract

Anhydrous potassium fluoride and ethyl α-bromophenylacetate in NN-dimethylformamide at 145–150° gave the corresponding α-fluoro-ester (53%), which was converted by alkaline hydrolysis and acidification, followed by reaction with thionyl chloride, into α-fluorophenylacetyl chloride (not isolated) and thence into the corresponding amide or NN-dimethylamide by conventional reactions. Diborane reduced the NN-dimethylamide to NN-dimethyl-2-fluoro-2-phenylethylamine (53%), also obtained by the action of dimethylamine on 1-bromo-2-fluoro-2-phenylethane. Reduction of the NN-dimethylamide with lithium aluminium hydride in ether gave a mixture of products.