5-Methoxytryptamine → Ammonium Hydroxide

Participants

Reaction Steps

Combine 3-phenoxybenzaldehyde (5.6 ml, 26.7 mmol), 5-methoxytryptamine (5.0 g, 26.7 mmol) and 3 Å molecular sieves (1.0 g) in methanol (50 ml) and under argon and heat at reflux for 4 hours. Remove the molecular sieves by filtration and then slowly add sodium borohydride (3.0 g, 60.0 mmol) portionwise. Stir at room temperature for 1 hour and concentrate under reduced pressure, dissolve the concentrated reaction mixture in sodium hydroxide 1N (100 ml) and extract with dichloromethane (3×50 ml). Combine organic layers and wash sequentially with distilled water (50 ml) and brine (50 ml), dry (Na2SO4) the organic layer, and concentrate to give a residue. Chromatograph the residue on silica gel eluting with 9:1 EtOAc:MeOH with 2% NH4OH gives the title compound.

Provenance & Evidence