The Gabriel synthesis of amines

by James

Description: The Gabriel synthesis is a method for making primary amines through an SN2 reaction of a phthalimide with an alkyl halide followed by cleavage with hydrazine (NH2NH2).
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{ 2 comments… read them below or add one }

Shirin Pillai

When would you use Gabriel vs Azide to make a primary amine in synthesis?



Great question! For uncomplicated molecules without a lot of different functional groups, they both work.

From a practical standpoint, N3- tends to get more use.

N3- tends to be a better nucleophile (faster rxn) than potassium phthalimide. Also, reduction of N3 to NH2 can be done many different ways (Pd-C/H2, LiAlH4, etc) and only blows off N2, whereas cleavage of the phthalimide necessitates getting rid of the byproduct.

For your purposes though – either one is probably fine!


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