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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1163909Generated: October 25, 2026

N-Ethyltryptamine → N-ethyl-N-(N-benzyloxycarbonylglycyl)-tryptamine

https://huagongshe.com/reaction/1163909

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN-EthyltryptamineHCID 6092—
ReactantTriethylamineHCID 8471—
ReactantBenzyloxycarbonylglycineHCID 14349—
ReactantIsobutyl chloroformateHCID 62365—
SolventTetrahydrofuranHCID 8028—
ProductN-ethyl-N-(N-benzyloxycarbonylglycyl)-tryptamineHCID 20513176101.6%

Reaction Conditions

Temperature-15 °C

Reaction Steps

30 ml of anhydrous tetrahydrofuran and 1.05 g of triethylamine are added to 2.17 g of N-benzyloxycarbonyl-glycine, and 1.43 g of isobutyl chloroformate are added dropwise thereto at -15° C. under stirring. A solution of 1.96 g of N-ethyl-tryptamin (i.e., 3-(2-ethylamino)ethylindole) in 40 ml of anhydrous tetrahydrofuran is added dropwise to the mixture at the same temperature, and said mixture is stirred at 0° C. for one hour and further stirred at room temperature for 16 hours. After the reaction, the reaction mixture is evaporated to remove solvent. The residue (oil) is purified by silica gel chromatography (Solvent: ethyl acetate-chloroform (1:1). 4.0 g of N-ethyl-N-(N-benzyloxycarbonylglycyl)-tryptamine are thereby obtained as a colorless oil. Yield: 100%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04367230
Source datasetuspto-grants-1983_01
ORD IDord-c07ad14976464c3099faf93d61d2dd8f
Source noteuspto-grants-1983_01