Sodium Iodide → N,alpha-Bis(4-fluorophenyl)-1-(2-naphthalenylmethyl)-4-piperidinemethanamine

Participants

Reaction Steps

A mixture of N,α-bis(4-fluorophenyl)-4-piperidinemethanamine (6.47 g, 0.0214 mol), 2-(bromomethyl)naphthalene (4.74 g, 0.0214 mol), and potassium carbonate (4.84 g, 0.035 mol) was heated 16 h at reflux in 400 mL of 1-butanol containing sodium iodide (0.2 g). The reaction mixture was concentrated to dryness. The residue was partitioned with 5% sodium hydroxide. The chloroform layer was dried (Na2SO4), filtered, and concentrated to give a dark brown oil. The oil was dissolved in methylene chloride and subjected to flash chromatography. Elution was accomplished using methylene chloride, 1% acetone-methylene chloride, 2% acetone-methylene chloride, 5% acetone-methylene chloride, and 10% acetone-methylene chloride. Fractions of similar purity were combined, and solvents were removed to give a viscous gum. This material was dried in vacuo 16 h at 100° C. in the presence of phosphorus pentoxide. This procedure provided 3.40 g (36%) of white glass-like material.

Provenance & Evidence