Methanol → 3,4-Didehydro naratriptan oxalate
Reaktionsgleichung
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)(=[O:5])=[O:4].[OH-:17].[K+].[CH3:19][N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1.[CH3:27][OH:28]>>[C:23]([OH:26])(=[O:4])[C:27]([OH:28])=[O:17].[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[C:23]1[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH:22]=1)(=[O:5])=[O:4]Komponenten
5
Versuchsvorschrift
A solution of N-methyl-1H-indole-5-ethanesulphonamide (1.0 g) in methanol (50 ml) containing potassium hydroxide (5.6 g) and N-methyl-4-piperidone (1.0 ml) was heated at reflux for 24h, cooled, and the resulting solid filtered off (1.0 g). A sample of the solid (0.2 g) was dissolved in a hot methanolic solution of oxalic acid (0.06 g), the solution cooled, and the salt precipitated by adding ethyl acetate (20 ml) and dry ether (50 ml). The salt was filtered off, and dried in vacuo to give the title compound as a solid (0.12 g) m.p. 87°-90° (shrinks) Analysis Found: C,52.2; H,5.6; N,9.5. C17H23N3O2S.C2H2O4.0.6H2O requires C,52.5; H,6.0; N,9.7%.
Aufarbeitung
- temperaturewas heated
- temperaturecooled
- filtrationthe resulting solid filtered off (1.0 g)
- dissolutionA sample of the solid (0.2 g) was dissolved in a hot methanolic solution of oxalic acid (0.06 g)
- temperaturethe solution cooled
- customthe salt precipitated
- additionby adding ethyl acetate (20 ml) and dry ether (50 ml)
- filtrationThe salt was filtered off
- customdried in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-36c743241eb8401dbd961db09df5d8c6
- Quelldatensatz
- uspto-grants-1991_03
- Patentnummer
- US04997841
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