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

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Reaction Steps

Concentrated hydrochloric acid (0.5 mL) was added to a solution of 1-(3-cyclohexyl-3-hydroxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine (670 mg, 1.4 mmol) obtained in Example 43 in THF (5 ml) and methanol (5 ml) and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure and the residue was made to basic with 10% aqueous potassium carbonate. The mixture was 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 crude product was treated with 4N hydrochloric acid in ethyl acetate solution and the title compound was crystallized from ethanol-diisopropyl ether to obtain 520 mg (yield 75%). mp. 220–222° C.

Provenance & Evidence