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

HRID 903593

Reaction equation

HRID 903593 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[CH2:2][CH2:3][CH2:4][C:5]([O:7]C)=O.[CH3:12][NH:13][CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1.Cl>>[CH3:12][N:13]([C:5](=[O:7])[CH2:4][CH2:3][CH2:2][C:1]([O:10][CH3:11])=[O:9])[CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6088MethyltryptamineHCID 14242Dimethyl Glutarate

Product 1

HCID 23336480N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamineYield 74.8%

Conditions

Temperature
150 °C

Procedure

8.0 g of dimethyl glutarate were added to 8.70 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole), and the mixture was heated at 150° C. under reduced pressure for 2 hours. 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 an aqueous saturated sodium chloride solution, successively. The washed extract was dried and evaporated under reduced pressure to remove solvent. The residue thus obtained was recrystallized from a mixture of ethyl acetate and n-hexane. 11.3 g of N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-methoxycarbonylbutanamido)ethyl]-indole) were thereby obtained. M.p. 101°-102° C. Yield: 70%

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. extractionThe washed extract
  4. customwas dried
  5. customevaporated under reduced pressure
  6. customto remove solvent
  7. customThe residue thus obtained
  8. customwas recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-6716595877b943c0bcbc809cc2a611a5
Source dataset
uspto-grants-1980_10
Patent number
US04228168

Linked notes

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