Formaldehyde → 1-(2-diethylaminomethyl-6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-6-phenylhexan-1-one

HRID 611174

Reaktionsgleichung

[O:1]1[C:9]2[CH2:8][CH2:7][N:6]([C:10](=[O:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:5][C:4]=2[CH:3]=[CH:2]1.[CH2:23]([NH:25][CH2:26][CH3:27])[CH3:24].[CH2:28]=O>C(O)(=O)C>[CH2:23]([N:25]([CH2:28][C:2]1[O:1][C:9]2[CH2:8][CH2:7][N:6]([C:10](=[O:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:5][C:4]=2[CH:3]=1)[CH2:26][CH3:27])[CH3:24]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of 0.347 g (1.167 mmol) of 1-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-6-phenylhexan-1-one in 20 ml of acetic acid, 0.14 ml (1.4 mmol) of diethylamine and 0.11 g (1.4 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 3 times. The combined organic layer was dried over anhydrous magnesium 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=4/1) to yield the desired product.

Aufarbeitung

distillationAfter the solvent was distilled off under reduced pressure
extractionextracted with dichloromethane 3 times
dry with materialThe combined organic layer was dried over anhydrous magnesium 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=4/1)

Quellen und Nachweise

ORD-Eintrag: ord-31c751a3a023403987b928739f55f562
Quelldatensatz: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05998433

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