Tryptamine → 1-(2,3-dihydro-5-benzofuranyl)-2,3,4,9-tetrahydro-1H-beta-carboline

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Reaction Steps

This product was prepared using a two-step procedure. A solution of tryptamine (32.4 g, 0.2 mol) and 2,3-dihydrobenzofuran-5-carboxaldehyde (30.0 g, 1 equiv.) in toluene (1 L) was heated under reflux for 4 hours. After removal of 4 mL of water and evaporation of toluene the residue was dissolved in DCM (1 L) in the presence of TFA (31 mL, 2 equiv.). The resulting mixture was stirred at rt for 16 hours. Then 1 L of a saturated aqueous solution of NaHCO3 was added. After extraction with DCM and drying over MgSO4, the organic solution was evaporated in vacuo. Recrystallization from DCM:iPr2O (2:30) gave the title compound as white crystals in a 80% yield.

Provenance & Evidence