Gabriel Synthesis for Primary Amines

Gabriel synthesis is a selective way to make primary amines. It avoids direct alkylation, which can create polyalkylated products. For that reason, it is a preferred method when the goal is to make only one alkylated amine product.

The reaction starts with phthalimide, which holds nitrogen in a p...

Recall that direct alkylation of ammonia gives a mixture of 1°-, 2°-, and 3°-amines. To exclusively make primary amines, phthalimide—a protected form of ammonia comprising only one acidic N–H proton capable of single alkyl substitution is used.

Gabriel synthesis uses phthalimide, a base, and hydrazine to convert alkyl halides into primary...