Réaction #76803

Équation de réaction

4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

ethylenediamine

→

title compound

4′-(N-2-Aminoethyl)aminospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

Conditions de réaction

Traitement

1. 1
   Températureto reflux under a nitrogen atmosphere
2. 2
   Autrethe solvent was removed in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 20 mL of saturated aqueous sodium carbonate
4. 4
   Extractionextracted with chloroform (3×25 mL)
5. 5
   ExtractionThe combined organic extract
6. 6
   Séchagewas dried over anhydrous magnesium sulfate
7. 7
   Concentrationconcentrated in vacuo

Mode opératoire

A solution of 74 mg (0.295 mmol) of 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] in 10 mL of ethylenediamine was heated to reflux under a nitrogen atmosphere and stirred for 4 days. Upon cooling to ambient temperature, the solvent was removed in vacuo. The residue was dissolved in 20 mL of saturated aqueous sodium carbonate and extracted with chloroform (3×25 mL). The combined organic extract was dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound as a dark oil, 80 mg (100%): electrospray MS (m/z, relative intensity) 275 ([MH]+).

Source