Potassium Hydroxide → HCID 20339677, compound

Participants

Reaction Steps

A mixture of 2.25 grams (5.38 mmol) of 2-(2,2,2-triphenylethyl)-1-azabicyclo[2.2.2]octane-3-one hydrochloride (XI), 1.14 grams (19.4 mmol) 85% H2NNH2.H2O, 1.5 grams (23 mmol) 85% KOH and 160 ml of diethylene glycol is heated to reflux for 2 hours. The resultant solution is cooled to room temperature and poured into 1.0 liter of ice-water. The aqueous layer has a pH of about 12.0 which is adjusted to about 14.0 with aqueous KOH. The solution is extracted twice with diethyl ether, and the combined ether extracts are shaken with dilute HCl (400 ml. containing 4 ml. of concentrated HCl) resulting in the formation of a fine solid precipitate. The precipitate is filtered and washed with water and diethyl-ether, and air-dried to provide 892 mg. of a white powder. The white powder is recrystallized from methanolether and dried in vacuo (0.1 mm. Hg) at 100° for 18 hours and then at 140° for 2 hours to provide the product, 2-(2,2,2-triphenylethyl)-1-azabicyclo[2.2.2]octane hydrochloride (VIII); MW:403.99.

Provenance & Evidence