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

HRID 1163909

Reaction equation

C(N(CC)CC)C.[CH2:8]([O:15][C:16]([NH:18][CH2:19][C:20]([OH:22])=O)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.ClC(OCC(C)C)=O.[CH2:31]([NH:33][CH2:34][CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1)[CH3:32]>O1CCCC1>[CH2:31]([N:33]([C:20](=[O:22])[CH2:19][NH:18][C:16]([O:15][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:17])[CH2:34][CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1)[CH3:32]

Participants

Conditions

Temperature: -15 °C

Procedure

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%.

Workup

additionare added dropwise
stirringis stirred at 0° C. for one hour
stirringfurther stirred at room temperature for 16 hours
customAfter the reaction
customthe reaction mixture is evaporated
customto remove solvent
customThe residue (oil) is purified by silica gel chromatography (Solvent

Sources & evidence

ORD record: ord-c07ad14976464c3099faf93d61d2dd8f
Source dataset: uspto-grants-1983_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04367230

Linked notes

Loading…