Dimethylamine → HCID 19599921, Verbindung

HRID 611164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 611164
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[CH:24]=[CH:23][C:11]([C:12]([N:14]3[CH2:19][CH2:18][C:17]4[O:20][CH:21]=[CH:22][C:16]=4[CH2:15]3)=[O:13])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:27][NH:28][CH3:29].[CH2:30]=O>C(O)(=O)C>[CH3:27][N:28]([CH2:30][C:21]1[O:20][C:17]2[CH2:18][CH2:19][N:14]([C:12](=[O:13])[C:11]3[CH:23]=[CH:24][C:8]([C:6](=[O:7])[C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:26][CH:25]=4)=[CH:9][CH:10]=3)[CH2:15][C:16]=2[CH:22]=1)[CH3:29]

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 19600137HCID 19600137, Verbindung

Produkt 1

HCID 19599921HCID 19599921, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 0.300 g (0.820 mmol) of 5-[4-(4-chlorobenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 20 ml of acetic acid, 0.11 ml (1.23 mmol) of 50% aqueous dimethylamine and 0.10 ml (1.23 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 120 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 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)

Quellen und Nachweise

ORD-Eintrag
ord-e2cb4a319e9e4609bdbc0bdb3b23f21c
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998433

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