View source for Forster–Decker method

{{Short description|Series of chemical reactions}}
The '''Forster–Decker method''' is a series of [[chemical reaction]]s that have the effect of mono-[[alkylation|alkylating]] a primary [[amine]] ('''1'''), forming a secondary amine ('''6''').<ref>{{Cite journal | last1 = Forster | first1 = Martin Onslow| author-link = Martin Onslow Forster| doi = 10.1039/CT8997500934 | title = XCI.–Influence of substitution on specific rotation in the bornylamine series | journal = [[Journal of the Chemical Society, Transactions]]| volume = 75 | pages = 934–935 | year = 1899 | url = https://zenodo.org/record/1763692}}</ref><ref>Decker, H.; Becker, P. ''Ann.'' '''1913''', ''395'', 362.</ref> The process occurs by way of transient formation of an [[imine]] ('''3''') that undergoes the actual alkylation reaction.

[[File:Forster-Decker Method Scheme.png|center|600px|The Forster-Decker method]]

==Process stages==
# Conversion of the primary amine to an imine (Schiff base) using an [[aldehyde]].<ref>{{cite book |last= McMurry |first= John |date= 1988 |title= Organic Chemistry |edition= Second |publisher= Brooks/Cole Publishing Company |page= 674-675|isbn= 0-534-07968-7}}</ref>
# Alkylation of the imine using an [[alkyl halide]], forming an [[iminium ion]].<ref>{{cite web |url=https://synarchive.com/named-reactions/forster-decker-amine-synthesis |title=Forster-Decker Amine Synthesis |author=<!--Not stated--> |date=2011–2022 |website=SynArchive.com The Organic Synthesis Archive |access-date=December 12, 2022}}</ref>
# [[Hydrolysis]] of the iminium, releasing the secondary amine and regenerating the aldehyde. <ref>{{cite web |url=https://www.chemistrysteps.com/imine-and-enamine-hydrolysis-mechanism/ |title=Imine and Enamine Hydrolysis Mechanism |author=<!--Not stated--> |date=2016–2022 |website=Chemistry Steps |access-date=December 13, 2022}}</ref>

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 reaction|S<sub>N</sub>2]]-type process can.

==See also==
* [[Reductive amination]]

==References==
{{Reflist}}

{{DEFAULTSORT:Forster-Decker method}}
[[Category:Substitution reactions]]
[[Category:Name reactions]]


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