Hydrochloric Acid → N-stearyl pyridone

Participants

Reaction Conditions

Reaction Steps

Into a 2 liter flask equipped with stirrer and temperature thermostat was charged octadecylamine (stearylamine, 18.9 grams, 0.07 mol; obtained from Sigma-Aldrich Co., Milwaukee, Wis.) followed with ethyl cyanoacetate (7.9 grams, 0.07 mol; obtained from Spectrum Chemicals, New Brunswick, N.J.). The resulting mixture was stirred and heated to 120° C. internal temperature for 1 hour. To the hot reaction mixture was then sequentially added ethyl acetoacetate (10.08 grams, 0.0775 mol; obtained from Lonza Group, Germany), piperidine (11.0 grams, 0.13 mol; obtained from Sigma-Aldrich Co.), and 60 milliliters of a solvent mixture containing 5 parts by weight toluene and 1 part by weight 1,2-dimethoxyethane. The reaction proceeded at 120° C. for another 24 hours. The solvents were then removed by distillation in vacuo, and the remaining viscous liquid was carefully poured into a solution of methanol (80 milliliters), deionized water (20 milliliters), and concentrated hydrochloric acid (16 milliliters, 2.5 mol). A solid precipitate formed instantly and the slurry was vacuum filtered followed by rinsing the solid cake with 2×50 milliliter portions of 80 percent aqueous methanol. The cake thus obtained was air-dried for 24 hours to afford 24.5 grams (0.061 mol, 87 percent yield) of N-stearyl pyridone product as light tan powder.

Provenance & Evidence