Triethylamine → N-[[4-(Tetradecyloxy)phenyl]methyl]benzamide

Participants

Reaction Steps

To a room temperature slurry of 2.01 g of nicotinoyl chloride hydrochloride in 25 ml of methylene chloride is added, via cannula, 3.0 g of product from Example 99 in 75 ml of methylene chloride. After 10 minutes, 3.8 g of triethylamine is added, dropwise, and the solution is stirred at room temperature for 20 hours. The reaction is poured into half saturated sodium bicarbonate and extracted with chloroform. The combined organic layers are washed with saturated sodium chloride and concentrated in vacuo. The residue is purified by chromatography (silica gel: 7.5% methyl alcohol/chloroform) and recrystallized from heptane/methyl alcohol to give 3.57 g of the desired product as pale yellow needles.

Provenance & Evidence