Réaction #76805

Équation de réaction

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

benzylamine

sodium carbonate

→

title compound

Rendement 34.0%

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

Rendement 34.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Températureto reflux under a nitrogen atmosphere
2. 2
   Extractionextracted with chloroform (3×25 mL)
3. 3
   ExtractionThe combined organic extract
4. 4
   Séchagewas dried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated in vacuo, and flash
6. 6
   Autrechromatographed on neutral silica gel using
7. 7
   workup.ADDITIONa 9:1 mixture of ammoniated chloroform/methanol

Mode opératoire

A solution of 97 mg (0.387 mmol) of 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] in 5 mL of benzylamine was heated to reflux under a nitrogen atmosphere and stirred for 18 hours. Upon cooling to ambient temperature, the diluted with 40 mL of water, basicified with 2 mL of saturated aqueous sodium carbonate and extracted with chloroform (3×25 mL). The combined organic extract was dried over anhydrous magnesium sulfate, concentrated in vacuo, and flash chromatographed on neutral silica gel using a 9:1 mixture of ammoniated chloroform/methanol to provide 42 mg (34%) of the title compound as a white solid: electrospray MS (m/z, relative intensity) 322 ([MH]+).

Source