Dimethylamine → HCID 19600003, Verbindung

HRID 611149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 611149
[O:1]1[C:5]2[CH2:6][N:7]([C:10](=[O:23])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH2:8][CH2:9][C:4]=2[CH:3]=[CH:2]1.[CH3:24][NH:25][CH3:26].[CH2:27]=O>C(O)(=O)C>[CH3:24][N:25]([CH2:27][C:2]1[O:1][C:5]2[CH2:6][N:7]([C:10](=[O:23])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH2:8][CH2:9][C:4]=2[CH:3]=1)[CH3:26]

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 19600184HCID 19600184, Verbindung

Produkt 1

HCID 19600003HCID 19600003, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 0.280 g (0.888 mmol) of 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-(4-fluorophenyl) hexan-1-one in 20 ml of acetic acid, 0.120 ml (1.33 mmol) of 50% aqueous dimethylamine and 0.108 ml (1.33 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate, 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 (chloroform/methanol=50/1 to 25/1) to yield the desired product.

Aufarbeitung

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 2 times
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (chloroform/methanol=50/1 to 25/1)

Quellen und Nachweise

ORD-Eintrag
ord-955d66bd04ff4101a9051cf000b3d550
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998433

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