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The Mannich Reaction

  1. F. F. Blicke

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or001.10

Organic Reactions

Organic Reactions

How to Cite

Blicke, F. F. 2011. The Mannich Reaction. Organic Reactions. 1:10:303–341.

Author Information

  1. University of Michigan

Publication History

  1. Published Online: 15 MAR 2011

Abstract

The Mannich reaction consists in the condensation of ammonia or a primary or secondary amines, usually as the hydrochloride, with formaldehyde and a compound containing at least one hydrogen atom of pronounced reactivity. The essential feature of the reaction is the replacement of the active hydrogen atom by an aminomethyl or substituted aminomethyl group. The product from acetophenone, formaldehyde, and a secondary amine salt is an example. The product to be expected from a Mannich reaction involving an ammonium salt is a primary amine. The mechanism of the Mannich reaction has not been established.

Keywords:

  • Mannich reaction;
  • secondary amines;
  • primary amines;
  • ammonia;
  • ketones;
  • aldehydes;
  • acids;
  • esters;
  • phenol;
  • picolines;
  • acetylenes;
  • quinaldines