p-Toluenesulfonic acid → N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamine

HRID 903597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 903597
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][N:13]([C:25](=[O:32])[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[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>CO>[CH3:12][N:13]([C:25](=[O:32])[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:1])=[O:30])[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

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 23336462N-methyl-N-(4-carboxybutyryl)-tryptamine

Produkt 1

HCID 23336480N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamineAusbeute 16.231 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

30 ml of methanol and 10 mg of p-toluenesulfonic acid were added to 2.88 g of N-methyl-N-(4-carboxybutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-carboxybutanamido)ethyl]-indole). The mixture was refluxed for 5 hours. After the reaction was completed, the mixture was concentrated to about 10 ml. The concentrated mixture was diluted with an aqueous saturated sodium bicarbonate solution under cooling and then extracted with ethyl acetate. The extract was washed with water, dried and then concentrated to dryness. The residue thus obtained was recrystallized from a mixture of ethyl acetate and n-hexane. 2.85 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: 95%

Aufarbeitung

  1. temperatureThe mixture was refluxed for 5 hours
  2. concentrationthe mixture was concentrated to about 10 ml
  3. additionThe concentrated mixture was diluted with an aqueous saturated sodium bicarbonate solution
  4. temperatureunder cooling
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated to dryness
  9. customThe residue thus obtained
  10. customwas recrystallized from a mixture of ethyl acetate and n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-6091593c3b1b4973a408cd8778348164
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04228168

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