Ethyl Nicotinate → HCID 20062134, compound

Participants

Reaction Steps

1-Bromo-6-[3-(octadecyloxy)propoxy]hexane obtained in Reference Example 4 (1.0 g) is heated with ethyl nicotinate (0.66 g) at 90° C. for 19 hours. After the reaction mixture is cooled, ether is added to the reaction mixture and the precipitate is collected by filtration to give 1-N-[6-[3-(octadecyloxy)propoxy]-hexyl]-3-ethoxycarbonylpyridinium bromide (1.0 g). To this compound in methanol (25 ml) is added with stirring 2N sodium hydroxide (4 ml), and the mixture is stirred at room temperature for 20 minutes. The reaction mixture is neutralized with 1 N hydrochloric acid, concentrated under reduced pressure, and extracted with dichloromethane. The extract is washed with an aqueous solution saturated with sodium chloride, dried and concentrated. The residue is subjected to purification by means of silica gel chromatography (chloroform-methanol-water= 65:25:4) and then to reprecipitation from chloroform-acetone to give the above-titled compound as pale yellow powder (0.63 g).

Provenance & Evidence