N,N-Diethylethylenediamine → HCID 88138733, compound

Participants

Reaction Steps

A solution of N,N-diethylethylenediamine (1.63 g, 0.014 mol) and 1,1'-carbonyldiimidazole (2.43 g, 0.015 mol) in 100 mL of tetrahydrofuran was stirred at room temperature under nitrogen for 2 h. A solution of N,α-bis(4-fluorophenyl)-4-piperidinemethanamine (3.76 g, 0.01245 mol) was added. The resulting solution was heated at reflux 16 h under nitrogen. The solution was cooled to room temperature and concentrated to dryness. The brown residue obtained was dissolved in methylene chloride. The methylene chloride layer was extracted with water, dried (Na2SO4), and filtered. The methylene chloride was removed with a rotary evaporator to give a dark brown oil (5.63 g). This material was dissolved in methylene chloride and placed on a silica gel column for flash chromatography. The column was eluted with 20% methanol-ethyl acetate, 50% methanol-ethyl acetate, and methanol. Fractions of similar purity were combined and solvents removed to give a dark brown oil. This material was dried for 16 h at 100° C. in the presence of phosphorus pentoxide. The procedure provided 4.21 g (74.2%) of a dark brown glass.

Provenance & Evidence