Piperazine → HCID 22375260, compound

Participants

Reaction Steps

To a solution of 2-cyclopenten-1-ol [cf. J. Org. Chem., 40, 1864 (1975)] (996 mg) and 2,4-dichloroquinazoline (2.36 g) in dimethylformamide (10 ml) is added 60% sodium hydride (in oil) (568 mg) with stirring at room temperature, and the mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with ethyl acetate, and washed with water 5 times. The ethyl acetate solution is dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. The resulting residue is briefly purified with medium pressure column chromatography (eluent, chloroform) to give a crystalline substance. The crystalline substance is added to a solution of piperazine (4.02 g) in dioxane (26 ml) with stirring at 70° C., and the mixture is stirred at the same temperature for one hour. The reaction mixture is diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. The resulting residue is purified by medium pressure liquid column chromatography (eluent, chloroform:methanol=10:1, 5:1, v/v) to give 4-[(cyclopent-2-en-1-yl)oxy]-2-(1-piperazinyl) quinazoline (1.57 g) as crystals.

Provenance & Evidence