Hydrochloric Acid → HCID 23368429, compound

Participants

Reaction Steps

To a suspension of 0.50 g of 3-(2-amino-3-methoxypropoxy)-5-chloro-1,2-benzoisoxazole and 0.5 g of 3,5-di-tert-butyl-4-hydroxybenzaldehyde in 5 ml of methanol is added 0.41 g of p-toluenesulfonic acid at 20°-25° C., and they are subjected to reaction at the same temperature for one hour. Subsequently, 0.13 g of sodium cyanoborohydride is added at 20°-25° C., and they are subjected to reaction at the same temperature overnight. Water and ethyl acetate are added to the reaction mixture and the pH is adjusted to 10 with a 10% (w/w) aqueous sodium hydroxide solution, after which the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The residue obtained is purified by a column chromatography [eluant:n-hexane:ethyl acetate=5:1], to obtain an oily product. The oily product obtained is dissolved in 10 ml of diethyl ether and 1 ml of water and to this solution is added 0.58 ml of a dioxane solution (2.2N) of hydrogen chloride, after which the crystals precipitated are collected by filtration and recrystallized from 50% ethanol, to obtain 0.27 g of colorless, crystalline 3-[2-(3,5-di-tert-butyl-4-hydroxybenzyl)amino-3-methoxypropoxy]-5-chloro-1,2-benzoisoxazole hydrochloride having a melting point of 191°-192° C.

Provenance & Evidence