Tryptamine → HCID 23366826, compound

Participants

Reaction Steps

A solution of 11.7 g (69.3 mmol) of carbonyldiimidazole and 5.0 g (69.3 mmol) of cyclopropylmethanol in 150 mL of THF was stirred, under nitrogen and later at room temperature for 4-5 hours or the time until the TLC (silica gel; hexane-ethylacetate, 4:1) analysis indicated a complete disappearance of cyclopropylmethanol in the mixture. To this reaction mixture, a solution of tryptamine (11.12 g, 69.3 mmol) in THF (5 mL) was added and stirred overnight. The TLC analysis indicated a complete disappearence of tryptamine. The solvent was removed and the residue was redissolved in methylene chloride (450 mL), washed with 5% HCl (4×100 mL), water, dried over MgSO4, filtered. The filtrate was swirled with 50 g of silica gel, filtered and concentracted under vacuum. The solid was crystallized from hexane-methylene chloride to furnish 13.6 g of N-cyclopropylmethyloxycarbonyltryptamine (75% yield). mp 88°-90° C.

Provenance & Evidence