2-Bromoethyl ethyl ether → HCID 19772014, compound

Participants

Reaction Steps

A mixture of N,α-bis(4-fluorophenyl)-4-piperidinemethanamine (3.33 g, 0.011 mol), 2-bromoethyl ethyl ether (1.69 g, 0.011 mol), and sodium bicarbonate (1.68 g, 0.011 mol) was stirred under nitrogen 16 h at room temperature. The mixture was then heated at reflux for 4 h and stirred 16 h at room temperature. The reaction was concentrated to dryness and partitioned between chloroform and water. The chloroform layer was back extracted with 5% sodium hydroxide. The chloroform layer was dried (Na2SO4), filtered, and the chloroform was removed to give an oil. The oil was subjected to flash chromatography on silica gel using methanol-methylene chloride mixtures for elution. Fractions of similar purity were combined and solvents removed. A brown oil was obtained which crystallized to a brown solid. This material was converted to the hydrochloride salt and the salt was recrystallized from methanol-diethyl ether to give a white solid. The solid was dried 16 h in vacuo at 78° C. This process furnished 2.00 g (39.8%) of white crystalline solid mp 241°-243° C. (dec.).

Provenance & Evidence