Chloroacetonitrile → 2-Benzyl-5-cyanomethyl-2,5-diazabicyclo[2.2.1]heptane

HRID 988955

Reaktionsgleichung

Reaktionsgleichung von HRID 988955
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]#[N:10].[CH2:11]([N:18]1[CH2:23][CH:22]2[CH2:24][CH:19]1[CH2:20][NH:21]2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[CH2:11]([N:18]1[CH2:23][CH:22]2[CH2:24][CH:19]1[CH2:20][N:21]2[CH2:8][C:9]#[N:10])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 5629322-Benzyl-2,5-diazabicyclo[2.2.1]heptane

Produkt 1

HCID 219636452-Benzyl-5-cyanomethyl-2,5-diazabicyclo[2.2.1]heptane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Finely ground potassium carbonate, as well as 1.3 mL of freshly distilled chloroacetonitrile were added to a solution of 3 g of 2-benzyl-2,5-diazabicyclo[2.2.1]heptane in 40 mL of anhydrous toluene and refluxed for 10 hours with vigorous stirring. The solution was cooled, filtered and evaporated. Bulb tube distillation (boiling point: 110°-120° C. at 0.01 mbar) resulted in 3.57 g of 140 as a colorless oil (97% of the theoretical yield).

Aufarbeitung

  1. temperaturerefluxed for 10 hours with vigorous stirring
  2. temperatureThe solution was cooled
  3. filtrationfiltered
  4. customevaporated
  5. distillationBulb tube distillation (boiling point: 110°-120° C. at 0.01 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-b74a3b1c9a3f4525a31d3bb55d105ccf
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638925B2

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