Octet / Reactions
Mannich Reaction
Mannich Reaction (Addition.) Converts CC(=O)C to CC(=O)CCN(C)C using HCHO, R₂NH (or NH₃), acid catalyst.
Addition
Reaction details
Name
Mannich Reaction
Type
Addition
Starting Material
CC(=O)C
Product
CC(=O)CCN(C)C
Reagents
HCHO
R₂NH (or NH₃)
acid catalyst
Mechanism
- Smiles
CC(=O)C
- Description
Enolizable ketone
- Smiles
C=NCC
- Description
Iminium ion forms from formaldehyde + amine
- Smiles
CC(=O)CCN(C)C
- Description
Enol attacks iminium → β-amino ketone (Mannich base)
Tips
Three-component reaction: C-H acid + aldehyde + amine
Product is β-amino carbonyl (Mannich base)
Important in alkaloid synthesis
Mannich base can undergo elimination to enone
Related Reactions
aldol-addition
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