1-Methylpiperazine → HCID 54410292, compound

Participants

Reaction Steps

N-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-5-benzylidenerhodanine(1.102 g., 0.002 mole) was added to a solution of N-methylpiperazine(2.40 g., 0.024 mole) in 50 ml. of methanol in a pressure bottle. The reaction mixture was stirred at room temperature for 18 hours. The mixture was filtered and the filtrate was evaporated to a brownish heavy syrup below 30° in vacuo. The residual syrup was dissolved in the minimum amount of acetone, and anhydrous ether was added to the solution to give a sticky precipitate. The supernatant was decanted, and the residual solid was dissolved in the minimum amount of methanol. Anhydrous ether was added to the solution to give a yellow precipitate. The solid was filtered, partially dissolved in ethyl acetate, and then chromatographed on a column of silica gel(1×20 cm) using ethyl acetate as the first solvent(50 ml.) and methanol as the second solvent(200 ml.). The 200 ml. of methanol effluent was reduced to ca. 20 ml. and was set aside at 5° for 24 hours. The white precipitate was filtered, washed with methanol, and dried at room temperature in vacuo, yielding 0.325 g.(50.6%); m.p. 175°-177°(dec.).

Provenance & Evidence