Delépine_reaction
The Delépine reaction is the organic synthesis of primary amines (4) by reaction of benzyl or alkyl halides (1) with hexamethylenetetramine (2) followed by acid hydrolysis of the quaternary ammonium salt (3).[1][2] It is named after the French chemist Stéphane Marcel Delépine (1871–1965).
Advantages of this reaction are selective access to the primary amine without side reactions from easily accessible reactants with short reaction times and relatively mild reaction conditions. Downsides include that the reaction is often performed using chloroform as solvent, which is toxic, and poor atom economy, including the formation of several equivalents of formaldehyde (a known carcinogen) during quaternary ammonium salt formation.[3]
An example is the synthesis of 2-bromoallylamine from 2,3-dibromopropene.[4]