Succinimide → HCID 68136841, compound

Participants

Reaction Steps

A mixture of 3.0 g. of cis-1-[p-(2,3-epoxypropoxy)phenyl]-6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalene, 0.80 g. of succinimide and 4 drops of piperidine in 100 ml. of absolute ethanol is heated under reflux for 17 hours. The resulting mixture is concentrated to approximately one-third volume by distillation under reduced pressure and the residue is diluted with water. The mixture so obtained is extracted with methylene chloride and the methylene chloride extract is washed with water and saturated sodium chloride solution before being evaporated to dryness. The residue is recrystallized from aqueous alcohol to yield cis-1-[p-(3-succinimido-2-hydroxy-propoxy)phenyl]-6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalene. The latter compound is then heated under reflux for 20 hours with a solution of 16 g. of sodium hydroxide in 320 ml. of ethanol. The resulting product is concentrated by distillation under reduced pressure and the residue is extracted with a mixture of methylene chloride and water. The methylene chloride solution is separated, washed with water, and taken to dryness. Hydrogen chloride is bubbled through a solution of the residue in ether. The solid which separates is isolated by filtration, and dried. There is thus obtained cis-1-[p-(3-amino-2-hydroxy-propoxy)phenyl]-6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride. The corresponding free base is obtained by dissolving the hydrochloride in methylene chloride, washing the resulting solution with an aqueous sodium bicarbonate solution, and evaporating the methylene chloride solution to dryness.

Provenance & Evidence