Hydrochloric Acid → HCID 70565280, compound

Participants

Reaction Steps

A stirred mixture of 1.7 g. of the product of Example 3, 14.0 g. of mossy tin 35 ml. of ethanol and 28.0 ml. of concentrated hydrochloric acid is heated under reflux for 48 hours. The reaction mixture is poured into dilute aqueous sodium hydroxide. This mixture is filtered and the filter cake is extracted with ethyl acetate. The extract is dried over magnesium sulfate and the solvent is evaporated to give 1.12 g. of a brown tar. The tar is dissolved in ethyl acetate, then the solution is treated with anhydrous hydrogen chloride to make it just acidic. A solid is formed and is collected. The material is dissolved in isopropyl alcohol, then hexane is added to precipitate a solid. The mixture is dissolved in water, made basic with aqueous sodium hydroxide solution and extracted with chloroform. The chloroform is dried over magnesium sulfate and concentrated to give a viscous liquid. The liquid is dissolved in ethyl acetate. The solution is made just acidic with anhydrous hydrogen chloride to provide a precipitate. The precipitate is collected to give cis-5,6,-dimethoxy-2-methyl-3-[2-(4-phenylpiperidino)ethyl]indoline dihydrochloride as cream-colored crystals, mp. 125°-132° C.

Provenance & Evidence