Tryptamine → N-(p-Methoxybenzyloxycarbonyl)tryptamine

Participants

Reaction Steps

To a suspension of 0.70 g (4.7 mmol) of tryptamine in 2.5 mL of deionized water and 0.65 mL (4.7 mmol) of triethylamine in a round bottom flask, equipped with an argon inlet, was added 1.45 g (4.7 mmol) of 2-(4-methoxybenzyloxycarbonyloxyimino)-2-phenylacetonitrile (MoZ-ON, Aldrich) in 5 mL of dioxane. During the first 5-10 minutes of stirring, the mixture became clear. This mixture was stirred for an additional 6 hours and diluted with 150 mL of saturated sodium chloride solution and extracted with 2×50 mL of ethyl acetate. The organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using hexane:ethyl acetate (1:1) as an eluent to yield (81%) N-(p-Methoxybenzyloxycarbonyl)tryptamine as white solid, mp. 108°-109° C.

Provenance & Evidence