Sodium Hydroxide → 3,4-Dihydrospiro[naphthalene-2(1H), 2'-piperidin]-1-one hydrochloride

Participants

Reaction Steps

In 250 ml of 1,2-dichloroethane was dissolved 7.64 g of 1-benzoyl-2-(2-phenylethyl)-2-piperidinecarbonitrile. To this solution was added 8.0 g of aluminum chloride and the mixture was refluxed for 6 hours. The reaction mixture was then cooled and poured cautiously into 10% aqueous sodium hydroxide and extracted with methylene chloride and water. The methylene chloride layer was dried over anhydrous sodium sulfate and filtered and the solvent was distilled off. To the group was added 100 ml of methanol and 100 ml of 20% aqueous sodium hydroxide and the mixture was refluxed for 12 hours. After cooling, methanol was distilled off and the group was extracted with methylene chloride and water. The methylene chloride layer was dried over anhydrous sodium sulfate and filtered and the solvent was distilled off. The group was purified by alumina column chromatography using ethyl acetate-hexane (1:2) as the eluent. The active fraction was concentrated under reduced pressure and the group was treated with 6.0 ml of 4N-methanolic hydrochloric acid to give a solid. This solid was recrystallized from methylene chloride to provide 3.0 g of colorless crystals.

Provenance & Evidence