Octane → HCID 86734416, compound

Participants

Reaction Conditions

Reaction Steps

To solution of 41 parts of α-(4-fluorophenyl)-2-pyridinylacetonitrile (U.S. Pat. No. 3,225,054) in 350 parts of dry toluene is added 9 parts of sodamide and the mixture is stirred and heated at 90° C for 30 minutes. Heating is stopped and a solution of 40 parts of 2-(2-chloroethyl)-2-azabicyclo[2.2.2.]octane in 110 parts of dry toluene is added slowly over a period of 30 minutes. The mixture is stirred and refluxed for 6 hours before it is cooled and decomposed by the addition of water. The toluene layer is separated and washed with water and extracted with 6N hydrochloric acid. The extract is made alkaline and extracted with toluene. The toluene solution is washed with water and dried and the solvent is evaporated. Distillation provides 2-(4-fluorophenyl)-2-(2-pyridyl-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile. According to the procedure of Example 1 this nitrile is converted to 5-[1-(4-fluorophenyl)-1-(2-pyridyl)-3-(2-azabicyclo[2.2.2]-oct-2-yl)propyl]-1H-tetrazole and in turn to 5-[1-(4-fluorophenyl)-1-(2-pyridyl)-3-(2-azabicyclo[2.2.2.] oct-2-yl)propyl]-1,3,4-oxadiazole having the following structural formula. ##STR34##

Provenance & Evidence