Diethylene Glycol → HCID 20339673, compound

Participants

Reaction Steps

9.3 Parts 3-(2,2-diphenylethyl-1-azabicyclo[2.2.2]-octan-3-one, 1.30 parts potassium hydroxide, 3.6 parts by volume of an 85% solution of hydrazine in water, and 59 parts diethylene glycol are combined and refluxed, with stirring, under nitrogen for 2.75 hours. Stirring and heating are then discontinued and the reaction mixture is allowed to stand for 16 hours at which time the mixture is heated to distill until a head temperature of 235° C. is reached. After cooling to room temperature, the mixture is partitioned between 900 parts by volume of a 5% sodium chloride solution and two 430 parts portions of ether. The ethereal extracts are combined, washed with water, dried over anhydrous sodium sulfate and stripped in vacuo to give an oil which solidifies upon standing. This solid is crystallized from n-pentane to afford, as a white solid, 2-(2,2-diphenylethyl)-1-azabicyclo[2.2.2]-octane, melting at about 87.5°-89.0° C. This compound is represented by the following structural formula. ##STR10##

Provenance & Evidence