Acetic Acid → HCID 9980864, compound

Participants

Reaction Steps

4-[5-Methoxy-2-(phenylethynyl)phenyl]-2-butanone (0.5 g, 1.8 mmole), the product of Example 1d, and homoveratryl amine (0.33 g 1.8 mmole) were combined in 10 mL of absolute methanol. With stirring, sodium cyanoborohydride (0.21 g, 3.3 mmole) was added in three portions. During this addition, the pH was adjusted to 6 with glacial acetic acid. After stirring for 5 hr, the reaction mixture was concentrated in vacuo and the resulting residue dissolved in methylene chloride. The methylene chloride solution was washed with 1N sodium hydroxide, water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 0.72 g of the title compound as a golden oil. The free base was dissolved in absolute methanol (5 mL) and treated with oxalic acid (0.2 g). After stirring for several hours, ether (50 mL) was added and the solution was cooled and filtered to give 1.0 g of the title compound as the oxalate salt.

Provenance & Evidence