Chloroform → HCID 67030555, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}thiophen-2-yl)propanoate (360.0 mg, 0.897 mmol) in anhydrous methanol (14 ml) was added hydrazine monohydrate (449 mg, 8.97 mmol), and the mixture was stirred at 45 to 50° C. for 2 days. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in 10% methanol-dichloromethane mixture and filtered through aminopropylated silica gel. The filtrate was concentrated under reduced pressure, and the residue was purified by aminopropylated silica gel column chromatography (2% methanol-dichloromethane mixture) to give a colorless oil. This was dissolved in anhydrous chloroform (30 ml), and 1M hydrogen chloride diethyl ether solution (4.0 ml, 4.0 mmol) was added dropwise. After stirring for 15 min, the reaction mixture was concentrated under reduced pressure. Anhydrous chloroform (30 ml) was added to the residue, and the mixture was concentrated under reduced pressure. This operation was repeated 3 times to removed excess hydrogen chloride azeotropically. The residue was suspended in anhydrous chloroform (30 ml), filtered, washed with anhydrous chloroform, anhydrous diethyl ether and ethyl acetate, and dried under reduced pressure to give the title compound (347.5 mg, yield 75.8%) as a slightly yellow white solid.

Provenance & Evidence