Halogen Containing Ketones, Esters and Carbinols Related to Methadone

Basic Amides as Antispasmodic Agents. Ii.

“…Alkylation of the substituted phenylacetonitriles with ßdialkylaminoethyl chlorides and sodium amide or lithium amide followed the procedures described for diphenylacetonitrile (1). The required nitriles were prepared as reported in the literature: «-phenylcapronitrile (4), cyclohexylidenephenylacetonitrile (5), 4-chlorodiphenylacetonitrile (6), and phenyl-a-pyridylacetonitrile (7). By analogy with the reaction of cyclohexylidenephenylacetonitrile with /3-piperidylethyl chloride (8), we assumed that the product from /S-dimethylaminoethyl chloride possessed the A^cyclohexenyl structure.…”

“…In view of the high anticholinergic action of the racemic -dimethylaminoa, -diphenylvaleramide (IV) (Centrine),5 6 it was thought that one enantiomorph might be physiologically more active, as is the case with methadone. Preparation of the two optically active isomers of IV was therefore undertaken.…”