Oxalyl chloride → 2-(2-(1-Piperidinyl)ethyl)pyridine

Participants

Reaction Steps

To a suspension of benzofurazan-5(or 6)-carboxylic acid (150 mg, 0.91 mmol) in methylene chloride (3.3 ml) was added dimethylformamide (1 drop) followed by dropwise addition of oxalyl chloride (89 μl, 1.0 mmol). The resulting solution was stirred at room temperature for 3 hours and then concentrated under reduced pressure. The brown oil was redissolved in methylene chloride (3.3 ml) and was added to a cooled (0° C.) solution of 4-(aminomethyl)-1-(2-pyridylethyl)piperidine (0.21 g, 0.95 mmol) in methylene chloride (1.6 ml). The reaction mixture was stirred at 0° C. for 11/2 hours. Solvent evaporation, flash chromatography (silica gel, chloroform-methanol-ammonium hydroxide, 95/5/1/2) and trituration with hexane-ethyl acetate gave 4-[N-benzofurazan-5(or 6)-carbonyl)aminomethyl]-1-(2-pyridylethyl)piperidine (133 mg, 40%); mp 149°-151° C.

Provenance & Evidence