Bromo N-Alkylation-百灵威

Bromo N-alkylation is the process by which an alkyl bromide reacts with an amine to form a higher substituted amine. The amine attacks the alkyl bromide in S_N2 fashion, releasing a bromide ion. Deprotonation yields the final product.

Lab Tips:

Multiple alkylations are likely to occur in excess alkyl halide leading to the production of quaternary ammonium salt.
Even with a limited amount of the alkyl halide, a mixture of products may be obtained.
If a monoalkylated amine product is desired, protocols for aldehyde reductive amination should be followed.

_{Carey, F.A., Sundberg, R.J. (2001). Advanced Organic Chemistry Part B: Reactions and Synthesis (4th ed.). New York: Kluwer Academic/Plenum Publishers.}

Reactant: Amine, Alkyl Bromide
Product: 2° or 3° Amine
Type of Reaction: S_N2
Bond Formation: C-N

Mechanism

Top Citations

Design of a Photoredox Catalyst That Enables the Direct Synthesis of Carbamate-Protected Primary Amines via Photoinduced, Copper-Catalyzed N-Alkylation Reactions of Unactivated Secondary Halides. J. Am. Chem. Soc. 2017, 139 (49), 18101–18106.

N-Alkylation of Amines with Alcohols Catalyzed by a Water-Soluble Cp*Iridium Complex: An Efficient Method for the Synthesis of Amines in Aqueous Media. Advanced Synthesis & Catalysis 2011, 353 (7), 1161–1168.

Photoinduced, Copper-Catalyzed Alkylation of Amines: A Mechanistic Study of the Cross-Coupling of Carbazole with Alkyl Bromides. J. Am. Chem. Soc. 2017, 139 (36), 12716–12723.

Related Reactions

Aldehyde Reductive Amination

Related Compounds

Amine

Alkyl Bromide

Alkyl Chloride