1-(3-Cyclohexylidene-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine hydrochloride → 1-(3-Cyclohexyl-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine

Participants

Reaction Steps

A mixture of 1-(3-cyclohexylidene-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine hydrochloride obtained in Example 45 (390 mg, 0.79 mmol), 10% palladium-carbon (300 mg) in ethanol (10 ml) and methanol (10 ml) was stirred at room temperature under hydrogen pressure of 4–5 atmospheres for 8 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was diluted with 10% aqueous potassium carbonate, and the aqueous layer was made alkaline and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=20/1) to obtain 95 mg (yield 26%) of the title compound via recrystallization (ethanol). mp. 119–121° C.

Provenance & Evidence