Synthesis

The most industrially significant amines are prepared from ammonia by alkylation in amine alkylation. Haloalkanes react with amines to give a corresponding alkyl-substituted amine, with the release of a halogen acid. Such reactions, which are most useful for alkyl iodides and bromides, are rarely employed because the degree of alkylation is difficult to control.

Nitriles are reduced to amines using hydrogen in the presence of a nickel catalyst, although acidic or alkaline conditions should be avoided to avoid hydrolysis of -CN group. LiAlH₄ is more commonly employed for the reduction of nitriles on the laboratory scale. Similarly, LiAlH₄ reduces amides to amines.

Aniline and its derivatives are prepared by reduction of the nitroaromatics. Many laboratory methods exist for the preparation of amines, many of these methods being rather specialized.

Reaction name	Substrate	Comment
Gabriel synthesis	organohalide	reagent: potassium phthalimide
Staudinger reduction	Azide	This reaction also takes place with a reducing agent such as lithium aluminium hydride.
Schmidt reaction	carboxylic acid
Aza-Baylis-Hillman reaction	imine	Synthesis of allylic amines
Hofmann degradation	amide	This reaction is valid for preparation of primary amines only. Gives good yields of primary amines uncontaminated with other amines.
Hofmann Elimination	Quaternary ammonium salt	upon treatment with strong base
Amide reduction	amides
Nitrile reduction	nitriles
Reduction of nitro compounds	nitro compounds	can be accomplished with elemental zinc, tin or iron with an acid.
Amine alkylation	haloalkane
Delepine reaction	organohalide	reagent hexamine
Buchwald-Hartwig reaction	aryl halide	specific for aryl amines
Menshutkin reaction	tertiary amine	reaction product a quaternary ammonium cation
hydroamination	alkenes and alkynes
Hofmann-Löffler reaction	haloamine