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The Forster–Decker method is a series of 
2. The next step is alkylation of the imine product to form iminium ion.
* Step F: Alkylation of imine product with X-R' where X = Cl, Br or I
3. The final step is hydrolysis of the iminium ion to form a secondary amine and regenerate the aldehyde starting material.
* Step G: Nucleophilic attack by a water molecule
* Step H: Proton transfers: shown in the mechanism using two molecules (water and acid) but this step might also be intramolecular
* Step I: Reformation of carbonyl and kicking out the secondary amine
* Step J: Deprotonation to regenerate aldehyde starting material
chemical reaction
A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the pos ...
s that transform a primary amine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...
(1) ultimately to a secondary amine (6). The first step is the formation of a Schiff base
In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure ( = alkyl or aryl, but not hydrogen). They can be considered a sub-class of imines, being either secondary ketimines or secondary aldimine ...
(3), followed by alkylation
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting ...
, and hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
.
Mechanism
1. The first step in the Forster-Decker Method is the formation of an imine (Schiff base) from a primary amine. * Step A: Nucleophilic attack on the aldehyde by a primary amine * Step B: Proton Transfer - creating carbinolamine * Step C: Protonation of hydroxyl oxygen of carbinolamine * Step D: Formation of iminium ion by losing water molecule * Step E: Deprotonation giving imine product
2. The next step is alkylation of the imine product to form iminium ion.
* Step F: Alkylation of imine product with X-R' where X = Cl, Br or I
3. The final step is hydrolysis of the iminium ion to form a secondary amine and regenerate the aldehyde starting material.
* Step G: Nucleophilic attack by a water molecule
* Step H: Proton transfers: shown in the mechanism using two molecules (water and acid) but this step might also be intramolecular
* Step I: Reformation of carbonyl and kicking out the secondary amine
* Step J: Deprotonation to regenerate aldehyde starting material
See also
*Reductive amination
Reductive amination (also known as reductive alkylation) is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is considered ...
References
Substitution reactions Name reactions {{Reaction-stub