The benzyl halide
1 reacts with hexamine to a
quaternary ammonium salt 3, each time just alkylating one nitrogen atom. Then the benzylammonium undergoes an acid-catalyzed hydrolysis process. : Depending on the hydrolysis conditions, the hexamine unit might instead break apart, leaving a benzyl amine (the
Delépine reaction). The reaction can also be applied to the oxidation of benzylic amines. In this way,
m-xylylenediamine can be converted to
isophthalaldehyde. ==References==