Tetrahydrofuran → 6-[6-[4-(Diphenylmethoxy)piperidino]hexyloxy][1,2,4]triazolo[1,5-b]pyridazine Fumarate

Participants

Reaction Steps

4-(Diphenylmethoxy)-1-piperidinehexanol (0.905 g) was dissolved in tetrahydrofuran (15 ml), followed by addition of 60% oily sodium hydride (118 mg). The mixture was refluxed under heating for 1 hour. After the mixture was cooled, 6-chloro[1,2,4]triazolo[1,5-b]pyridazine (381 mg) was added thereto. This mixture was refluxed under heating for hours, followed by addition of addition of ice-water and extraction with ethyl acetate. The extract was washed with an aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with a mixture of ethyl acetate, methanol and triethylamine (50:5:1). Fractions containing the objective compound were collected and concentrated. The residue was dissolved in ethyl acetate (10 ml), followed by addition of a solution of fumaric acid (263 mg) in methanol (10 ml). The mixture was concentrated, and the residue was recrystallized from ethyl acetate to yield the title compound (0.979 g).

Provenance & Evidence