Ethylenediamine → 4'-(n-2-Aminoethyl)aminospiro[1-azabicyclo[2.2.2]octane-3,2'(3'h)-furo[2,3-b]pyridine]

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Reaction Steps

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]+).

Provenance & Evidence