Glutaraldehyde → 9-Benzyl-9-azabicyclo[3.3.1]nonan-3-one

HRID 1946854

Reaktionsgleichung

Reaktionsgleichung von HRID 1946854
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH:5]=[O:6].Cl.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:17]([C:24](O)=O)[C:18](CC(O)=O)=O.C([O-])(=O)C.[Na+]>O>[CH2:9]([N:16]1[CH:3]2[CH2:2][CH2:1][CH2:24][CH:17]1[CH2:18][C:5](=[O:6])[CH2:4]2)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 3485GlutaraldehydeHCID 68328Acetonedicarboxylic acidHCID 517045Sodium AcetateHCID 2724127Benzylammonium chloride

Produkt 1

HCID 4195319-Benzyl-9-azabicyclo[3.3.1]nonan-3-oneAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution in water (400 ml) of pentandial (84.5 g) and benzylamine hydrochloride (36.3 g), cooled at 0° C. 30.8 g of 1,3-acetonedicarboxylic acid are added. 70 ml of an aqueous solution of sodium acetate at 10% are then added. The obtained mixture is kept under stirring at room temperature for one hour and then heated for 4 hours to 50° C. The mixture is then acidified at pH 2 with a 10% w. HCl aqueous solution and then washed with diethyl ether. The pH is then brought to 6 with sodium bicarbonate and the aqueous phase extracted with dichloromethane. The organic extracts are anhydrified on sodium sulphate and the solvent evaporated to obtain 38.5 g of the compound 9-benzyl-9-azabicyclo[3.3.1]nonan-3-one (6a) as a light coloured solid.

Aufarbeitung

  1. temperatureheated for 4 hours to 50° C
  2. washHCl aqueous solution and then washed with diethyl ether
  3. extractionthe aqueous phase extracted with dichloromethane
  4. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-9432a7418fb6441ca9514fe24eb8b7ae
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399457B2

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