Synthesis of primary amines
Potassium phthalimide is a -NH2-synthon which allows the preparation of primary amines by reaction with alkyl halides. After alkylation, the phthalimid is not nucleophile and does not react anymore. Product is cleaved by reaction with base or hydrazine, which leads to a stable cyclic product.
Mechanism of the Gabriel Synthesis
Note: Phthalimide is acidic!
Organic Reactions in Ionic liquids: N-Alkylation of Phthalimide and Several Nitrogen Heterocycles
Z.-G. Le, Z.-C. Chen, Y. Hu, Q.-G. Zheng, Synthesis, 2004, 208-212.
A convenient Two-Step Procedure for the Synthesis of Substituted Allylic Amines from Allylic Alcohols
S. E. Sen, S. L. Roach, Synthesis, 1995, 756-758.