p-Toluenesulfonic acid → HCID 18967779, Verbindung

HRID 399624

Reaktionsgleichung

Reaktionsgleichung von HRID 399624
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]1([C:18]([CH:20]2[CH2:22][CH2:21]2)=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:23]([NH2:26])[CH2:24][CH3:25]>C1(C)C=CC=CC=1>[CH:20]1([CH:18]([NH:26][CH2:23][CH2:24][CH3:25])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:22][CH2:21]1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 7852PropylamineHCID 77029Cyclopropyl phenyl ketone

Produkt 1

HCID 18967779HCID 18967779, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

4 Å molecular sieves and 100 mg of paratoluenesulphonic acid are added to 10 g of cyclopropyl phenyl ketone in 60 ml of anhydrous toluene, followed by 6 g of propylamine. Imine formation is monitored by gas chromatographic assay. After heating for 6 hours at 55° C., the reaction mixture is cooled, the molecular sieves are filtered off and the solution is evaporated to dryness under vacuum. The residue is taken up in 100 ml of anhydrous ethanol. The solution is cooled to 0° C. and 2.65 g of sodium borohydride are added portionwise. After stirring overnight at room temperature, the mixture is evaporated to dryness under vacuum and the residue is taken up in water, hydrolysed with 1N hydrochloric acid in order to bring the pH to 2, and washed with ethyl acetate. The pH is brought to 9 by addition of 2N sodium hydroxide and the mixture is then extracted several times with methylene chloride.

Aufarbeitung

  1. temperaturethe reaction mixture is cooled
  2. filtrationthe molecular sieves are filtered off
  3. customthe solution is evaporated to dryness under vacuum
  4. temperatureThe solution is cooled to 0° C.
  5. addition2.65 g of sodium borohydride are added portionwise
  6. customthe mixture is evaporated to dryness under vacuum
  7. washwashed with ethyl acetate
  8. additionThe pH is brought to 9 by addition of 2N sodium hydroxide
  9. extractionthe mixture is then extracted several times with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-7bf037825dc44434ac0527981cefa234
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05821255

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