Dimethylformamide → 9-Benzyl-7-methoxy-1-methyl-beta-carboline

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Reaction Steps

Harmine 1 (2.1 g, 10 mmol), DMF (50 ml) and THF (50 ml) were respectively added in a 250 ml round-bottom flask, and were stirred at room temperature for 10 minutes followed by the addition of 60% NaH (1.2 g, 30 mmol). The mixture was stirred until there were no bubbles formed. Benzyl bromide (3 ml) was added dropwise. The mixture was then refluxed by heating for 8 h. THF was evaporated in reduced pressure, and the residues were poured into cold water. The mixture was adjusted to pH 3.0 with concentrated HCl, and extracted with ethyl ether. The aqueous phase was neutralized (pH8) with saturated NaHCO3 solution and extracted with ethyl acetate. The organic phases were combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered, evaporated in reduced pressure and then recrystallized with ethyl acetate to afford gray crystals (2.2 g, 67%). mp 131-133° C.

Provenance & Evidence