Naphthalene → 2-Naphthyl 4-piperidyl ketone hydrochloride

Beteiligte Stoffe

Reaktionsschritte

To a slurry of 99 g of naphthalene (0.75 mole) and 96 g of isonipecotic acid chloride hydrochloride (0.5 mole) in tetrachloroethane is added over a period of 10 minutes 200 g (1.5 moles) of aluminum chloride. The reaction mixture is allowed to stand at room temperature for 10 minutes, then decomposed by pouring it over ice water, made basic with a 50% NaOH solution, and extracted with diethyl ether. The ether layer is dried over magnesium sulfate, filtered, and treated with ethereal HCl. The resulting oil is dissolved in warmed methanol, treated with charcoal, filtered and diluted with butanone. The methanol is removed by distillation, adding more butanone as needed. The solution is cooled overnight, and the resulting solid filtered off and recrystallized from methanol-butanone to give the desired product. M.P. 251°-253° C.

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