The Gabriel synthesis is named for the German chemist Siegmund Gabriel. Traditionally, it is a chemical reaction that transforms primary alkyl halides into primary amines using potassium phthalimide.
The Gabriel reaction has since been generalized to include the alkylation of sulfonamides and imides, followed by deprotection, to obtain amines (see #Alternative Gabriel reagents).
The utility of the method is based on the fact that the alkylation of ammonia is an unselective and inefficient route to amines in the laboratory (on an industrial scale, the alkylation of ammonia is, however, widely employed). The conjugate base of ammonia, sodium amide (NaNH2), is more basic than it is nucleophilic. In fact, sodium amide is used to deliberately obtain the dehydrohalogenation product.
Read more about Gabriel Synthesis: Traditional Gabriel Synthesis, Alternative Gabriel Reagents
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