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This compound is a reagent used in the Gabriel synthesis of amines.
He discovered the Gabriel Synthesis in 1887.
This scission reaction allows phthalimide anion to be used as amine precursor in the Gabriel synthesis.
Saccharin can be used to prepare exclusively disubstituted amines from alkyl halides via a Gabriel synthesis.
The Gabriel synthesis is named for the German chemist Siegmund Gabriel.
The Gabriel synthesis, involving the use of an equivalent to NH, only applies to primary alkyl halides.
The Gabriel synthesis of amines is an example of extremely low atom economy, as stochiometric quantities of phthalic acid derivatives are formed.
Amines may also be prepared from alkyl halides in amine alkylation, the Gabriel synthesis and Delepine reaction, by undergoing nucleophilic substitution with potassium phthalimide or hexamine respectively, followed by hydrolysis.
Potassium phthalimide, made by reacting phthalimide with potassium carbonate in water at 100 C or with potassium hydroxide in absolute ethanol, is used in the Gabriel synthesis of primary amines, and the Gabriel synthesis of glycine has yields as high as 85%.
