Potassium Iodide → 4-[4-[alpha-(p-Tert-butylphenyl)-alpha-hydroxybenzyl]piperidino]butyrophenone hydrochloride

Participants

Reaction Steps

A mixture of 12 g (0.0372 mole) of α-phenyl-α-(p-tert-butylphenyl)-4-piperidinemethanol, 7.85 g (0.042 mole) of 4-chlorobutyrophenone, 13.8 g (0.1 mole) of potassium carbonate, and 0.1 g of potassium iodide in 100 ml of toluene is refluxed with stirring for 64 hours. Upon cooling to room temperature the mixture is filtered, and to the filtrate is added an equal volume of ether followed by treatment with ethereal HCl. The resulting precipitate is recrystallized from isopropyl alcohol and from methanolbutanone to give 4-[4-[α-hydroxy-α-(p-tert-butylphenyl)benzyl]piperidino]butyrophenone hydrochloride, M.P. 228°- 230°C.

Provenance & Evidence