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

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Reaction Steps

Harmine 1 (0.53 g, 2.5 mmol), DMF (15 ml) and THF (15 ml) were respectively added in a 100 ml round-bottom flask, and stirred at room temperature until the mixture became clear, then 60% NaH (0.3 g, 7.5 mol) was added and stirred until there were no bubbles formed. 1-Brombenzenepropropane (2 ml) was added dropwise. The mixture was refluxed for 12 h. THF was evaporated in reduced pressure. The residues were poured into 30 ml cold water and extracted with ethyl acetate. The organic phases were combined, and washed with water and brine, dried over anhydrous sodium sulfate, filtered, evaporated in reduced pressure, and the residue dissolved in 50 anhydrous ethanol. The pH was adjusted to 4 with concentrated HCl, the mixture were concentrated in vacuum and then recrystallized with acetone to afford yellow solids. The solids were dissolved into a mixed solution of water and ethyl acetate. The pH was adjusted to 8 with saturated NaHCO3 solution. The organic layer was isolated, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with water and brine, dried over anhydrous sodium sulfate, decolorized with activated carbon, filtered, concentrated, and recrystallized with ethyl ether to afford gray needle crystals (0.42 g, 51%), mp 117-118° C.

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