Chapter 22: Amines

Reductive Amination via Imines

Summary

• Aldehydes and ketones react (chapter 17) with  1^o amines to give substituted imines and 2^o amines to give enamines

These N species can then be reduced to amines.

The method provides access to 1^o, 2^o, or 3^o amines.

Typical reagents : step 1 : acidic buffer  step 2 :  most commonly catalytic hydrogenation (e.g. H₂/Pd)

Sodium cyanoborohydride (NaBH₃CN) (which is like NaBH₄) can be used for smaller scale reductions.

R, R' and R" may be either hydrogen, alkyl, or aryl.

• Reduction of Aldehydes and Ketones
• Reduction of Alkenes

© Dr. Ian Hunt, Department of Chemistry