Warning: Amines (and ammonia) are good nucleophiles, but are not generally useful for preparing primary amines because of rampant over-alkylation.

Note: Primary amines can be prepared by reduction of nitriles.

Note: Primary amines can be prepared by reduction of nitro groups.

Note: Gabriel synthesis of primary amines starts with deprotonation of phthalimide to produce a good nucleophile.

Note: Gabriel synthesis of primary amines includes a typical Sn2 reaction against an unhindered alkyl halide, using the deprotonated phthalimide as the nitrogen nucleophile. Note that further (over) alkylation is not a problem for this product.

Note: The final step of Gabriel synthesis of a primary amine is hydrolysis of the phthalimide. This is comparable to hydrolysis of an amide to an amine and carboxylic acid.

Note: Primary amides can be reduced to primary amines.

Note: Higher order amides can be reduced to form higher order amines.

Note: Reductive amination couples amines and carbonyls (aldehydes and ketones). This is essentially a 2-step reaction with initial condensation of the amine and carbonyl to form an imine, which the reducing agent then converts into a secondary amine.

Note: Reductive amination with a secondary amine yields a tertiary amine via an iminium ion intermediate.

Note: Hofmann elimination of amines to alkenes. Refer to the [Mechanism] for more details on the initial 'exhaustive methylation' of the amine to form a decent leaving group out of a quarternary ammonium salt, followed by E2 elimination by hydroxide ion.

Note: Hofmann elimination is distinctive for producing the anti-Zaitsev product. In other words, it is regioselective to produce the least substituted alkene.