Hydrochloric Acid → HCID 19019400, compound

Participants

Reaction Conditions

Reaction Steps

7.2 g (15 mMole) 1-Benzyl-2-hydroxymethoxy-5octadecyloxy-4(1H)-pyridone are dissolved in 110 mL anhydrous dimethylformamide at 70° C. and mixed portionwise with 0.60 g (20 mMole) sodium hydride (80% in paraffin oil). After subsequently stirring for 1.5 hours at 70 to 80° C., a solution of 3.3 g (27.15 mMole) 3-dimethylaminopropyl chloride in 20 mL anhydrous dimethylformamide is added dropwise thereto. The reaction mixture is then stirred for 2 hours at 70° C. Thereafter, the solution is evaporated to dryness under vacuum and the residue is mixed with water and dichloromethane. The organic phase is separated off, dried over anhydrous sodium sulphate and evaporated. The residue is chromatographed on a column of silica gel with dichloromethane/methanol saturated with gaseous ammonia (97:3 v/v), an oily substance being obtained. 1.8 g (3.3 mMole) of this substance are dissolved in a mixture of 30 mL ethyl acetate and 3,5 mL propan-2-ol and mixed with diethyl ether saturated with gaseous hydrogen chloride for salt formation. The precipitated salt is recrystallized from ethyl acetate/propan-2-ol (3:1 v/v), colorless crystals being obtained; m.p. 155°-159° C. The solid material contains about 1/4mole of water per mole of the said product.

Provenance & Evidence