Acetone → Indecainide

HRID 1262509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1262509
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1([C:18]([NH2:20])=[O:19])[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.C(O)C.[CH3:24][C:25]([CH3:27])=O.[H][H]>[Pd].C(OCC)(=O)C>[CH:25]([NH:1][CH2:2][CH2:3][CH2:4][C:5]1([C:18]([NH2:20])=[O:19])[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)([CH3:27])[CH3:24]

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 702EthanolHCID 127612DeisopropylindecainideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 52195Indecainide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 6.7 g. of 9-(3-aminopropyl)-9-aminocarbonylfluorene (prepared as described in Example 29) in 90 ml. of ethanol containing 1.6 g. of acetone was stirred at 40° C. for sixteen hours. The reaction mixture was then hydrogenated for two hours at ambient temperature in the presence of 2.0 g. of 5% palladium on carbon and hydrogen at a pressure of 60 psi. The reaction mixture next was filtered and the solvent was removed from the filtrate by evaporation to provide a foam. The foam was dissolved in ethyl acetate and then extracted into 1N hydrochloric acid. The aqueous acid layer was separated, made alkaline with 50% sodium hydroxide, and the product was extracted into fresh ethyl acetate. The organic extracts were combined, washed with water, dried, and the solvent was removed by evaporation under reduced pressure to provide 9-(3-isopropylaminopropyl)-9-aminocarbonylfluorene identical to that obtained in Example 27.

Aufarbeitung

  1. filtrationThe reaction mixture next was filtered
  2. customthe solvent was removed from the filtrate by evaporation
  3. customto provide a foam
  4. extractionextracted into 1N hydrochloric acid
  5. customThe aqueous acid layer was separated
  6. extractionthe product was extracted into fresh ethyl acetate
  7. washwashed with water
  8. customdried
  9. customthe solvent was removed by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ccc676e140794258bda4350ec25b5584
Quelldatensatz
uspto-grants-1984_06
Patentnummer
US04452745

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