2-Bromo-2'-acetonaphthone → 2-[4-(alpha-Hydroxy-p-fluorobenzyl)piperidinyl]-2'-acetonaphthone

Participants

Reaction Steps

5.4 g of 2-bromo-2'-acetonaphthone, 4.6 of 4-(α-hydroxy-p-fluorobenzyl)piperidine and 10 g of sodium hydrogencarbonate were refluxed in ethanol solvent for 2.5 h. After completion of the reaction, the product was treated by an ordinary process. The obtained oily product was purified according to silica gel column chromatography to obtain 5 g of 2-[4-(α-hydroxy-p-fluorobenzyl)piperidinyl]-2'-acetonaphthone; 1 g of this product was stirred together with 1.0 g of acetic anhydride and 0.1 g of dimethylaminopyridine in pyridine solvent at room temperature for 5 h. After completion of the reaction, the oily product was purified according to silica gel column chromatography and converted into its hydrochloride, which was recrystallized from ethyl acetate and methanol.

Provenance & Evidence