N-alkylation

N-alkylation forms a carbon–nitrogen bond by attaching an alkyl group to a nitrogen atom. It occurs in organic synthesis and in biological pathways.

Nucleophilic substitution: A reaction in which a nucleophile replaces a leaving group bonded to an electrophilic atom. Alkyl halides commonly undergo substitution when nitrogen attacks their carbon atom.
Amine: An organic compound derived from ammonia by replacing one or more hydrogen atoms with carbon groups. Amines are common nitrogen substrates for N-alkylation.
Alkylation of heterocycles: The attachment of alkyl groups to atoms in aromatic or nonaromatic heterocyclic compounds. Ring nitrogens in heterocycles are frequent targets for selective alkylation.
N-acylation: The attachment of an acyl group to a nitrogen atom. An acyl group contains a carbonyl; an alkyl group does not.
Menshutkin reaction: A reaction in which a tertiary amine alkylates to form a quaternary ammonium salt. It is a clear case of direct nitrogen attack on an alkyl halide.
Alkyl group: A saturated hydrocarbon substituent formed by removing one hydrogen atom from an alkane. Its transfer to nitrogen defines the transformation.
N-methylation: The introduction of a methyl group onto a nitrogen atom. Methyl transfer is a common, specific form of N-alkylation.
O-alkylation: The attachment of an alkyl group to an oxygen atom. Competing oxygen attack can divert alkylation from nitrogen in ambident substrates.
Reductive amination: A method for making amines by forming an imine or iminium ion and then reducing it. It installs an alkyl group on nitrogen through carbonyl condensation followed by reduction.
Leaving group: An atom or group that departs with an electron pair during a chemical reaction. Leaving-group ability strongly affects substitution-based N-alkylation.

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