Dimethylamine → 2-dimethylaminomethyl-5-(6-phenylhexyl)-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

HRID 611430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 611430
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][C:16]3[O:19][CH:20]=[CH:21][C:15]=3[C:14]2=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][NH:24][CH3:25].[CH2:26]=O>C(O)(=O)C>[CH3:23][N:24]([CH2:26][C:20]1[O:19][C:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:14](=[O:22])[C:15]=2[CH:21]=1)[CH3:25]

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196001085-(6-phenylhexyl)-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

Produkt 1

HCID 195999812-dimethylaminomethyl-5-(6-phenylhexyl)-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 0.242 g (0.814 mmol) of 5-(6-phenylhexyl)-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one in 10 ml of acetic acid, 0.37 g (4.1 mmol) of 50% aqueous dimethylamine and 0.33 g (4.1 mmol) of 37% aqueous formaldehyde were added, followed by overnight refluxing. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with ethyl acetate 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

  1. temperaturerefluxing
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. extractionextracted with ethyl acetate 3 times
  4. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. 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-ee78eaa981214c4ba4ca988292073ab4
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998433

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