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Dimethylamine → N,N-dimethyl-[6-[4-(2-methylbenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

HRID 611271
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 611271
[CH3:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([C:6]1[CH:22]=[CH:21][C:9]([C:10]([N:12]2[CH2:17][CH2:16][C:15]3[CH:18]=[CH:19][O:20][C:14]=3[CH2:13]2)=[O:11])=[CH:8][CH:7]=1)=[O:5].[CH3:27][NH:28][CH3:29].[CH2:30]=O>C(O)(=O)C>[CH3:27][N:28]([CH2:30][C:19]1[O:20][C:14]2[CH2:13][N:12]([C:10](=[O:11])[C:9]3[CH:21]=[CH:22][C:6]([C:4](=[O:5])[C:3]4[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=4[CH3:1])=[CH:7][CH:8]=3)[CH2:17][CH2:16][C:15]=2[CH:18]=1)[CH3:29]
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Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196000596-[4-(2-Methylbenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Produkt 1

HCID 19599918N,N-dimethyl-[6-[4-(2-methylbenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 0.250 g (0.724 mmol) of 6-[4-(2-methylbenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 10 ml of acetic acid, 0.098 ml (1.09 mmol) of 50% aqueous dimethylamine and 0.088 ml (1.09 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 magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1) 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 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/methanol=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-17cf343580ad4c549c03b301eadace28
Quelldatensatz
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05998433

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