Reductive Amination of Aldehydes and Ketones (Carbonyls)
Aldehydes and ketones can be converted into 1o, 2o and 3o amines using reductive amination. The reaction takes place in two parts. The first step is the nucleophiic addition of the carbonyl group to form an imine. The second step is the reduction of the imine to an amine using an reducing agent. A reducing agent commonly used for this reaction is sodium cyanoborohydride (NaBH3CN).
The nitrogen gains a bond to carbon during this reaction sequence. When carbonyls react with ammonia, a primary amine is produced. The reaction pattern continues for each amine classification. For example, pyrrolidine reacts with 2-butanone to produce the imine, which can be reduced by LiAlH4, sodium cyanoborohydride (NaBH3CN), or H2 with an active metal catalyst to produce a tertiary amine.
Amide Reduction to 1°, 2° or 3° Amines using LiAlH4
8. Add the missing reactants/products to the following reactions.
Prof. Steven Farmer (Sonoma State University)
Jim Clark (Chemguide.co.uk)