Benzaldehyde → 1-Phenyl-2,3,4,9-tetrahydro-1H-beta-carboline

Participants

Reaction Steps

A mixture of 1.0 g (6.24 mmol) of tryptamine and 0.73 g (0.87 mmol) of benzaldehyde in 10 ml of acetic acid was refluxed for 3 hours. After completion of the reaction, the solvent was distilled off, and the residue was made alkaline by the addition of a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and then the solvent was removed by evaporation under reduced pressure to give 1.82 g of a crude mixture. The resulting residue was subjected to column chromatography using 35 g of silica gel with a 9:1 by volume mixture of methylene chloride and methanol as the eluent, to yield 1.43 g (92%) of the title compound. The product was subsequently recrystallized from dichloroethane and hexane to yield 0.72 g of pale yellowish brown crystals.

Provenance & Evidence