4-Pyridinecarboxaldehyde → (+/-)-7-(4-Pyridylmethyleneamino)-1,2,3,5,6,7,8,8a-octahydroindolizine

HRID 9873

Reaktionsgleichung

Reaktionsgleichung von HRID 9873
[NH2:1][CH:2]1[CH2:10][CH:9]2[N:5]([CH2:6][CH2:7][CH2:8]2)[CH2:4][CH2:3]1.[CH:11]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=O.S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[N:16]1[CH:17]=[CH:18][C:13]([CH:11]=[N:1][CH:2]2[CH2:10][CH:9]3[N:5]([CH2:6][CH2:7][CH2:8]3)[CH2:4][CH2:3]2)=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 133894-PyridinecarboxaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21988494Octahydroindolizin-7-amine

Produkt 1

HCID 21988493(+/-)-7-(4-Pyridylmethyleneamino)-1,2,3,5,6,7,8,8a-octahydroindolizineAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(±)-7-Amino-1,2,3,5,6,7,8,8a-octahydroindolizine (4.91 g (35.0 mmol), prepared as described in 1)) was dissolved in toluene (95 ml). To the solution were added 4-formylpyridine (3.34 ml, 35.0 mmol) and anhydrous magnesium sulfate (3.75 g, 31.2 mmol), and the resulting mixture was stirred at 70° C. for 3 hours. At the end of this time, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated by evaporation under reduced pressure, to give the title compound (8.08 g) as a pale yellow oil (yield quantitative).

Aufarbeitung

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-48980c3bc29d442994e424cd77e71dc8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091352B2

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