4-(4-Chlorophenyl)-4-hydroxypiperidine → HCID 22111000, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (1.4 g) and 4-(4-chlorophenyl)-4-hydroxypiperidine (1.3 g) in xylene (10 mL) was stirred under nitrogen gas at 120° C. for 1.5 hours and, then, refluxed for 16 hours. Thereafter, 0.85 g of 4-(4-chlorophenyl)-4-hydroxypiperidine was added and the mixture was refluxed for 24 hours. After cooling, the reaction mixture was filtered and washed with diethyl ether. The filtrate was extracted with 1N-hydrochloric acid and the aqueous layer was made weakly acidic with saturated aqueous sodium hydrogen carbonate (NaHCO3). This aqueous layer was washed with diethyl ether and made weakly basic with saturated aqueous NaHCO3. This solution was extracted with ethyl acetate and the organic layer was washed with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from diethyl ether/hexane to provide 0.58 g of the title compound. Yield 28%.

Provenance & Evidence