Hydrochloric Acid → N-ethyl-N-(4-methoxycarbonylbutyryl)-tryptamine

HRID 903585Notes

Reaction equation

HRID 903585 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)[CH3:2].[CH3:15][O:16][C:17]([CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23])=[O:18].Cl>N1C=CC=CC=1>[CH2:1]([N:3]([C:22](=[O:23])[CH2:21][CH2:20][CH2:19][C:17]([O:16][CH3:15])=[O:18])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6092N-EthyltryptamineHCID 73916Methyl 4-chloroformylbutyrate

Product 1

HCID 23336475N-ethyl-N-(4-methoxycarbonylbutyryl)-tryptamineYield 74.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

10 g of N-ethyl-tryptamine (i.e., 3-(2-ethylaminoethyl)-indole) were dissolved in 80 ml of pyridine, and 9.62 g of 4-methoxycarbonylbutyryl chloride were added dropwise thereto at 10° C. The mixture was stirred for one hour. After the reaction was completed, the mixture was acidified with dilute hydrochloric acid and then extracted with ethyl acetate. The extract was washed with water, an aqueous saturated sodium bicarbonate solution and water, successively. The washed extract was dried and evaporated under reduced pressure to remove solvent. The oily residue thus obtained was recrystallized from a mixture of ethanol and petroleum ether. 12.5 g of N-ethyl-N-(4-methoxycarbonylbutyryl)-tryptamine (i.e., 3-[2-(N-ethyl-4-methoxycarbonylbutanamido)ethyl]-indole]were thereby obtained as yellow crystals. M.p. 73°-75° C. Yield: 74.4%

Workup

  1. customat 10° C
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. extractionThe washed extract
  5. customwas dried
  6. customevaporated under reduced pressure
  7. customto remove solvent
  8. customThe oily residue thus obtained
  9. customwas recrystallized from a mixture of ethanol and petroleum ether

Sources & evidence

ORD record
ord-585b1100524d4a40a75b6c7e87f5f443
Source dataset
uspto-grants-1980_10
Patent number
US04228168

Reaction notes

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