1-Methyl-4-piperidone → 1-Acetyl-7-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-1,2,3,5-tetrahydropyrrolo [2,3-f]indole
Reaktionsgleichung
[C:1]([N:4]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][NH:13][C:14]=3[CH:15]=[C:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:16][N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.C[O-].[Na+]>CO>[C:1]([N:4]1[C:8]2=[CH:9][C:10]3[C:11]([C:20]4[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH:19]=4)=[CH:12][NH:13][C:14]=3[CH:15]=[C:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred suspension of 1-acetyl-1,2,3,5-tetrahydropyrrolo[2,3-f]indole (J. Med. Chem. 1995, 38, 2524) (1.60 g, 8 mmole) and 1-methylpiperidin-4-one (1.81 g, 16 mmole) in dry methanol (70 ml) was added sodium methoxide (2.59 g, 48 mmole). The mixture was heated at reflux under argon for 24 hours, then cooled and concentrated by evaporation to approx. 25% volume; then treated with water (5 ml), stirred and the solid precipatate collected by filtration. The solid was suspended in ethanol (20 ml), heated to boiling, cooled and filtered to leave the title compound as a pale cream powder (1.20 g).
Aufarbeitung
- temperatureThe mixture was heated
- temperatureat reflux under argon for 24 hours
- temperaturecooled
- concentrationconcentrated by evaporation to approx. 25% volume
- additionthen treated with water (5 ml)
- filtrationthe solid precipatate collected by filtration
- temperatureheated
- temperaturecooled
- filtrationfiltered
Quellen und Nachweise
- ORD-Eintrag
- ord-74365394984e413f8761ce14b4f09e0b
- Quelldatensatz
- uspto-grants-2002_05
- Patentnummer
- US06391891B1
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