Aniline → N-phenyl-5-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-amine

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Reaction Conditions

Reaction Steps

Aniline (120 mg, 1.29 mmol) and p-toluenesulfonic acid monohydrate (25.0 mg, 0.131 mmol) were added to a solution of 5-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-ol (260 mg, 0.656 mmol) obtained in Reference Example 18 in methanol (3 ml) and the mixture was stirred at 60° C. for 120 hours. The resulting mixture was concentrated under reduced pressure. The residue was made to basic with 1N aqueous potassium carbonate 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 basic column chromatography (hexane then hexane/ethyl acetate=25/1) to obtain 270 mg (yield 87%) of the title compound via recrystallization (methanol). mp. 90–94° C.

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