piperidine-4-carbonyl chloride;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of 3.15 g (19.4 mmoles) of 2-chloronaphthalene and 4.46 g (24.2 mmoles) of 4-piperidinecarbonyl chloride hydrochloride in 60 ml nitrobenzene is added gradually 9.7 g (73 mmoles) of aluminum chloride. The mixture is heated to 65°-70° C. for 2 hours and cooled. Ice water and concentrated HCl are added to the reaction mixture. The solid precipitate is partitioned between aqueous sodium hydroxide solution and ether and the organic phase washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue is recrystallized from cyclohexane to yield 6-chloro-2-naphthyl 4-piperidyl ketone. M.P. 98°-100°-5°. The mixture is heated to 65°-70° C. for 2 hours cooled The solid precipitate is partitioned between aqueous sodium hydroxide solution and ether the organic phase washed with brine dried over Na2SO4 concentrated in vacuo The residue is recrystallized from cyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. extracted with diethyl ether The ether layer is dried over magnesium sulfate filtered treated with ethereal HCl The resulting oil is dissolved in warmed methanol treated with charcoal filtered diluted with butanone The methanol is removed by distillation adding more butanone The solution is cooled overnight the resulting solid filtered off recrystallized from methanol-butanone