Hydrochloric Acid → HCID 20144933, compound

Participants

Reaction Conditions

Reaction Steps

86.4 g of 1-benzyl-4-piperidinol in 200 ml. and dimethylformamide are added dropwise to a stirred suspension of 34.7 g of a 50% oil dispersion of sodium hydride in 900 ml. of dimethylformamide at 60°-70° C. When no more hydrogen gas is liberated, a mixture of 68.4 g of p-difluorobenzene in 200 ml. of dimethylformamide is added slowly, and the temperature is raised to 80° C. Stirring and heating is continued for 48 hours, the reaction is cooled, poured into 2 l. of water, and the aqueous suspension is extracted with benzene. The benzene extracts are dried and the benzene is removed under reduced pressure, leaving a thick brown oil. The oil solidifies on standing. The solid is dissolved in 95% ethanol, the solution is filtered and the solvent is removed from the filtrate, leaving a yellow oil. The oil is dissolved in absolute ethanol, the solution is stirred, and saturated ethereal-HCl is added. A resultant hydrochloride salt precipitates out of solution and is collected and dried. The salt is recrystallized from an ethanol and ether mixture to give 1-benzyl-4-(p-fluorophenoxy)piperidine hydrochloride.

Provenance & Evidence