The Forster–Decker method is a series of chemical reactions that have the effect of mono-alkylating a primary amine (1), forming a secondary amine (6). The process occurs by way of transient formation of an imine (3) that undergoes the actual alkylation reaction.
Process stages
- Conversion of the primary amine to an imine (Schiff base) using an aldehyde.3
- Alkylation of the imine using an alkyl halide, forming an iminium ion.4
- Hydrolysis of the iminium, releasing the secondary amine and regenerating the aldehyde. 5
Because the actual alkylation occurs on the imine, over-alkylation is not possible. Therefore, this method does not suffer from side-reactions such as formation of tertiary amines as a simple SN2-type process can.
See also
References
Forster, Martin Onslow (1899). "XCI.–Influence of substitution on specific rotation in the bornylamine series". Journal of the Chemical Society, Transactions. 75: 934–935. doi:10.1039/CT8997500934. /wiki/Martin_Onslow_Forster ↩
Decker, H.; Becker, P. Ann. 1913, 395, 362. ↩
McMurry, John (1988). Organic Chemistry (Second ed.). Brooks/Cole Publishing Company. p. 674-675. ISBN 0-534-07968-7. 0-534-07968-7 ↩
"Forster-Decker Amine Synthesis". SynArchive.com The Organic Synthesis Archive. 2011–2022. Retrieved December 12, 2022. https://synarchive.com/named-reactions/forster-decker-amine-synthesis ↩
"Imine and Enamine Hydrolysis Mechanism". Chemistry Steps. 2016–2022. Retrieved December 13, 2022. https://www.chemistrysteps.com/imine-and-enamine-hydrolysis-mechanism/ ↩