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).
Content available for Reactionguide members only. Not a member? Get access for about 30 cents / day!

{ 2 comments… read them below or add one }

Shirin Pillai November 21, 2014 at 10:50 pm

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

Reply

James December 2, 2014 at 7:29 am

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!

Reply

Leave a Comment