1,2-Dichloroethane → 2-Phenyl-2-(3-pyridyl)-4-chlorobutyronitrile

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Reaction Steps

A solution of 19.3 parts of α-phenyl-3-pyridylacetonitrile in 140 parts by volume of dry benzene is treated with 4 parts of soda amide and the mixture is refluxed with stirring for 1 hour. The mixture is cooled to room temperature and ethylene dichloride 17.2 parts is added. The mixture is stirred and refluxed for 4 hours, cooled, washed with water and dried. Removal of solvent and isolation provides 2-phenyl-2-(3-pyridyl)-4-chlorobutyronitrile. Following the procedure set out in Example 9, 8.9 parts of 4-hydroxy-4-phenylpiperidine are reacted in 400 parts by volume of ethylene glycol monoethyl ether at reflux for 18 hours to provide 2-phenyl-2-(3-pyridyl)-4-(4-hydroxy-4-phenyl)piperidinobutyronitrile. Also following the procedures in Example 9 the latter compound is converted to 5-1-(phenyl)-1-(3-pyridyl)-3-[4-(4-hydroxy-4-phenyl)piperidino]propyl-1H-tetrazole and in turn to 5-1-(phenyl)-1-(3-pyridyl)-3-[4-(4-hydroxy-4-phenyl)piperidino]propyl-1,3,4-oxadiazole having the following structural formula ##STR46##

Provenance & Evidence