Methanol → HCID 20701369, compound

Participants

Reaction Steps

(E)-N-(3,4-dimethoxyphenethyl)-N-methyl-3-(3-pyridyl)-2-propenoic acid amide (2.65 g, 8.31 mmol) obtained in Example 84 was dissolved in dichloromethane (66 ml) and 1M boron tribromide-dichloromethane solution (33 ml) was dropwise added under argon at −30° C. and stirred for 14 hours. After methanol was added at the same temperature to stop the reaction, the solvent was distilled out under reduced pressure and hydrogen chloride/methanol solution was added to the residue and heated and refluxed for 1 hour. The solvent was distilled out under reduced pressure and potassium hydroxide/methanol solution was added to the residue to neutralize. The precipitated inorganic salts were filtered out and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=30:1) and recrystallized to yield the titled compound (2.19 g, 90%).

Provenance & Evidence