Tryptamine → HCID 23366813, compound

Participants

Reaction Steps

A solution of 1,1'-carbonyldiimidazole (2.03 g, 12.5 mmol), p-trifluoromethylbenzyl alcohol (2.2 g, 12.5 mmol) and THF (100 mL) was stirred for 2 hours. The reaction was monitored by TLC (silica gel, hexane:ethylacetate; 2:1) to examine the complete disappearence of p-trifluoromethylbenzyl alcohol. To this solution, 2.0 g (12.5 mmol) of tryptamine was added and the mixture was stirred overnight. The reaction contents were diluted with methylene chloride (100 mL). The organic layer was washed with 5% 3×100 mL of HCl, water (3×100 mL) and dried over anhydrous MgSO4. Upon evaporation of the solvent, under vacuum, crude N-(para-Trifluoromethylbenzyloxycarbonyl)tryptamine was obtained as a solid which was crystallized from ether-hexane mixture (2.6 g, 57% yield). mp 92°-94° C.

Provenance & Evidence