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

Participants

Reaction Steps

A solution of tryptamine (15 g, 94.0 mmol) and benzaldehyde (10.9 g, 1.1 eq.) in CH2Cl2 (800 mL) was treated with TFA (15 mL, 2 eq.). The resulting mixture was stirred at room temperature (rt) for one day and then neutralized to pH 7 with a saturated aqueous solution of sodium carbonate (Na2CO3). After filtration and concentration to dryness, the residue was recrystallized from 2-propanol to give the title compound (11.0 g, 47%) as white crystals (m.p.:175-177° C.).

Provenance & Evidence