Dimethylamine → 1-(2-dimethylaminomethyl-5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)decan-1-one
Reaktionsgleichung
[O:1]1[C:5]2[CH2:6][N:7]([C:10](=[O:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:8][CH2:9][C:4]=2[CH:3]=[CH:2]1.[CH3:21][NH:22][CH3:23].[CH2:24]=O>C(O)(=O)C>[CH3:21][N:22]([CH2:24][C:2]1[O:1][C:5]2[CH2:6][N:7]([C:10](=[O:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:8][CH2:9][C:4]=2[CH:3]=1)[CH3:23]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
To a solution of 0.230 g (0.829 mmol) of 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)decan-1-one in 20 ml of acetic acid, 0.090 ml (1.0 mmol) of 50% aqueous dimethylamine and 0.080 ml (1.0 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 1.5 hours. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=9/1) to yield the desired product.
Aufarbeitung
- distillationAfter the solvent was distilled off under reduced pressure
- extractionextracted with dichloromethane 2 times
- washThe combined organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=9/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-b80f8df76bc24eec947d5671771f0015
- Quelldatensatz
- uspto-grants-1999_12
- Patentnummer
- US05998433
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