Hydrochloric Acid → HCID 19772045, compound

Participants

Reaction Steps

A mixture of N,α-bis(4-fluorophenyl)-4-piperidinemethanamine (3.30 g, 0.0109 mol), benzylbromide (1.86 g, 0.0109 mol), and sodium bicarbonate (1.68 g, 0.02 mol) was stirred 16 h at room temperature in 300 mL of acetonitrile (dried over 4 A molecular sieves) containing sodium iodide (0.2 g). The mixture was then heated at reflux 16 h followed by stirring 72 h at room temperature. The reaction was stripped to dryness and partitioned between chloroform and water. The chloroform layer was extracted with 5% sodium hydroxide and dried (Na2SO4). The chloroform was removed to give a fluffy-brown residue. This material was dissolved in methylene chloride for flash chromatography on a silica gel column. Elution was accomplished using 1% acetone in methylene chloride, 3% acetone in methylene chloride, and 5% acetone in methylene chloride. Fractions of similar purity were combined, and solvents removed to give an oil. This oil was converted to the HCl salt in an ethanol-diethyl ether mixture. The white solid obtained was then recrystallized from methanol-diethyl ether to give a white solid. The solid was dried 16 h at 78° C. in the presence of phosphorus pentoxide. This method provided 1.86 g (36.7%) of white crystalline solid, mp 241°-242° C. (dec.).

Provenance & Evidence