Putrescine → 5-[N-(4-pentafluoropropionamidobutan-1-yl)aminomethyl]imidazo[1,2-a]pyridine

Participants

Reaction Steps

A suspension of 15.13 g (69.69 mmol) of 5-chloromethylimidazo[1,2-a]pyridine.hydrochloride and 12.29 g (139.38 mmol) of 1,4-diaminobutane in 150 ml of acetonitrile was heated for one hour under reflux while stirring. The reaction mixture was cooled to room temperature. The resulting precipitates of 1,4-diaminobutane.dihydrochloride were filtered off. To the filtrate were added 20.61 ml (139.38 mmol) of ethyl ester of pentafluoropropionic acid and 19.43 ml (139.38 mmol) of triethylamine. The mixture was stirred for one hour at room temperature. The solvent was then distilled off under reduced pressure, and the residue was extracted with 200 ml of dichloromethane. The organic layer was washed with 150 ml of a saturated aqueous saline solution, dried over magnesium sulfate, and distilled off the solvent. The residue was purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1) to afford 13.61 g of the desired compound (53.6%, a pale yellow liquid).

Provenance & Evidence