Isopropanol → HCID 21094261, compound

Participants

Reaction Steps

To a stirred solution of 2-(5-amino-3-pyridyl)-1-azabicyclo[2.2.2]octane trihydrochloride (50 mg, 0.16 mmol) in dry isopropanol (5 mL) was added isoamyl nitrite (0.1 mL, 0.97 mmol) and the reaction mixture was refluxed for 2 h. When TLC analysis of the reaction mixture showed the absence of starting material, the mixture was allowed to warm to ambient temperature and then the solvent was removed under vacuum. A white solid was obtained upon the addition of dry diethyl ether. The solid was dissolved with heating in a minimum amount of chloroform, and the solution kept over night at 4° C. to induce crystallization. The solid thus obtained was filtered and dried under vacuum for 24 h to afford 2-(5-isopropoxy-3-pyridyl)-1-azabicyclo[2.2.2]octane dihydrochloride (28 mg, 55%) as colorless needles.

Provenance & Evidence