In the presence of a catalytic acid or base, a β-amino carbonyl compound (called a Mannich base) is generated from an amine (1°or 2°), a non-enolizable carbonyl, and an enolizable carbonyl compound. Under acidic conditions, the amine reacts with the protonated non-enolizable carbonyl compound, forming an iminium ion. The enolized carbonyl compound then attacks the iminium ion in an aldol-type reaction, affording the Mannich base.

• Reagents: Catalytic Acid or Base, Solvent (Usually EtOH, MeOH, H₂O, or HOAc)
• Reactant: Ammonia, 1° or 2° Amine or its Hydrochloride, Non-Enolizable Aldehyde or Ketone, Enolizable Carbonyl Compound
• Product: β-Amino Carbonyl Compound (Mannich Base)
• Type of Reaction: Condensation

Mechanism

Original Paper

Top Citations

Related Reactions

Related Compounds