1-methyl-3,5-bis(2,3,4-trimethoxybenzylidene)-4-piperidinone synthesis

Yield:1049971-16-5 95%

Reaction Conditions:

with sodium hydroxide in water at 20;Aldol Condensation;

Steps:

4.4 _General procedure for synthesis of compounds 24-47 and 49-77 [47]

General procedure: To a solution of the aromatic aldehyde (10mmol, 2 equiv.) dissolved in 10mL of ethanol was added the appropriate ketone (5mmol, 1 equiv) such as acetone (compounds 24-47), cyclohexanone (compounds 49-63), or N-methylpiperidone (compounds 64-77) and stirred for 15min. Sodium hydroxide (0.4g) dissolved in water (10mL) was added and the resulting mixture was stirred at room temperature overnight. The separated solid was filtered, washed with cold ethanol and recrystallized from ethanol or ethanol/water.

References:

Deck, Lorraine M.;Hunsaker, Lucy A.;Vander Jagt, Thomas A.;Whalen, Lisa J.;Royer, Robert E.;Vander Jagt, David L. [European Journal of Medicinal Chemistry,2018,vol. 143,p. 854 - 865]