Methanesulfonic Acid → HCID 88800164, compound

Participants

Reaction Steps

A solution of 4-(2-chloro-9-xanthenylidene)piperidine (2.0 g., 6.75 mmol) in 5 ml. of acetic anhydride is heated on a steam bath for 2.5 hours. Acetone (30 ml.) and 50 ml. and 20% aqueous potassium carbonate is added to the cooled solution and the mixture stirred for one hour. Additional water is added and the mixture is extracted with ether. The extract is washed with 1N hydrochloric acid, water and dried. The solvent is evaporated to give the crude amide, 2.2 g. (recrystallized amide m.p. 165°-166° C.). The amide is dissolved in 500 ml. of ether and added to a stirred suspension of 2.0 g. of lithium aluminum hydride in 200 ml. of ether. After two hours at 23° C. excess hydride is decomposed with water (4 ml.) and 10% sodium hydrixode (3.2 ml.). The mixture is filtered and the filtrate is evaporated. The residue is dissolved in a mixture of methanol and ether and treated with one equivalent of methanesulfonic acid. The precipitated salt is filtered and recrystallized from methanol/ether to give 4-(2-chloro-9-xanthenylidene)-1-ethylpiperidine methanesulfonate, m.p. 249°-252° C.

Provenance & Evidence