Melatonin → HCID 15382325, Verbindung

HRID 370055

Reaktionsgleichung

Reaktionsgleichung von HRID 370055
[CH3:1][C:2]([NH:4][CH2:5][CH2:6][C:7]1[C:11]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=2[NH:9][CH:8]=1)=[O:3].[H-].[Na+].[C:20](Cl)(=[O:22])[CH3:21].[O:24]1CC[CH2:26][CH2:25]1>>[C:20]([N:9]1[C:10]2[C:11](=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[C:7]([CH2:6][CH2:5][NH:4][C:2](=[O:3])[CH3:1])=[CH:8]1)(=[O:22])[CH3:21].[C:20]([N:9]1[C:10]2[C:11](=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[C:7]([CH2:6][CH2:5][N:4]([C:25]([CH3:26])=[O:24])[C:2](=[O:3])[CH3:1])=[CH:8]1)(=[O:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 896MelatoninHCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydride

Produkt 2

HCID 15382325HCID 15382325, VerbindungHCID 44359266N-[2-(1-acetyl-5-methoxyindol-3-yl)ethyl]diacetamide

Versuchsvorschrift

Melatonin (126 mg) is dissolved in tetrahydrofuran (10 ml) in a 50 ml round-bottomed flask, sodium hydride (200 mg) is then added and the mixture is maintained at reflux (10 min). After cooling (0° C.), acetyl chloride is added and the mixture is kept stirring overnight (room temperature). After filtration and dilution (EtOAc), the organic phase is washed with water and then separated on a silica plate. N-[2-(1-Acetyl-5-methoxyindol-3-yl)ethyl]acetamide (1) is mainly obtained, along with a side product, N-[2-(1-acetyl-5-methoxyindol-3-yl)ethyl]diacetamide (10) (cf. Example 10).

Aufarbeitung

  1. temperaturethe mixture is maintained
  2. temperatureat reflux (10 min)
  3. additionis added
  4. filtrationAfter filtration and dilution (EtOAc)
  5. washthe organic phase is washed with water
  6. customseparated on a silica plate

Quellen und Nachweise

ORD-Eintrag
ord-707afcc28a634645995c8dc135c38eae
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140372

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