1,1-Dibromoethane → 10-[3-(N,N-diethylamino)propyl]-5-methyl-5H-pyrido[3,4-f]pyrrolo-[1,2-b] [1,2,5]triazepine

Participants

Reaction Conditions

Reaction Steps

To magnesium turnings (1.9 g) in 10 ml of diethyl ether and 10 ml of tetrahydrofuran, was added a solution of 11.66 g of 3-diethylaminopropyl chloride in 10 ml of tetrahydrofuran. The reaction was initiated by the addition of 1 ml of dibromoethane and the application of heat. After stirring at 70° C. for four hours, the reaction mixture cooled to room temperature and treated, dropwise, with a solution of 7.7 g of 5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine in 50 ml of tetrahydrofuran. The mixture was then stirred at room temperature for two hours, poured into an iced ammonium chloride solution, and extracted with ethyl acetate (3×). The combined extracts were washed with water followed by a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated. High pressure liquid chromatography of the concentrate (silica gel; elution with 15% methanol/dichloromethane) afforded 10-[3-(N,N-diethylamino)propyl]-5-methyl-5H-pyrido[3,4-f]pyrrolo-[1,2-b] [1,2,5]triazepine as an oil. The oil was dissolved in ethanol and acidified with an ethanol solution of fumaric acid. Diluting with diethyl ether precipitated 3.05 g of the corresponding sesquifumarate salt, mp 170°-172° C.

Provenance & Evidence