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Ainley and King Synthesis

(Ainley-King-Sargent Synthesis)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr007

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Ainley and King Synthesis. Comprehensive Organic Name Reactions and Reagents. 7:25–28.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

Ainley and King synthesis is a multistep synthesis of α-piperidyl-4-quinolinemethanols (or quinolyl-4-α-piperidylcarbinols). This reaction played an important role in the preparation of large quantities of quinine for antimalarial during the World War II. This reaction has been modified by various researchers. The Claisen-Geuther ester condensation in this synthesis has been optimized to a great extent by replacement of sodium ethoxide with sodium or sodium amide. Beside this, the cyclization to form the piperidinyl ring is carried out in a two-phase solvent system (H2O and ether) using sodium carbonate as base. It has been reported that lepidine can be easily isolated, if the preparation of lepidine at the stage of dehalogenation is performed in warm alcoholic KOH in the presence of Raney nickel. On account of these modification, formation of quininic acid via oxidation in acetone is also reported to be superior.

Keywords:

  • α-piperidyl-4-quinolinemethanols;
  • lepidine;
  • Raney nickel;
  • quininic acid