Hydrochloric Acid → N,alpha-bis(4-fluorophenyl)-1-(3-phenyl-2-propenyl)-4-piperidinemethanamine dihydrochloride hemihydrate

Participants

Reaction Steps

A mixture of 3.41 g (11.3 mmol) of the N,α-bis(4-fluorophenyl)-4-piperidinemethanamine, 1.85 g (12.1 mmol) of cinnamyl chloride, and 2.00 g (19.0 mmol) of sodium carbonate in 300 mL of acetonitrile was stirred at room temperature overnight. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and dilute NaOH. An insoluble residue was removed by filtration. The CH2Cl2 solution was subjected to flash chromatography (silica gel, eluted with 3% CH3OH in CH2Cl2) to give an oil. This was converted to the HCl salt, and the salt was recrystallized from CH3OH/ether to give 1.83 g (32.7%) as a white crystalline solid, mp 239°-241° C.

Provenance & Evidence