Hydrogen Bromide → HCID 20217855, compound

Participants

Reaction Steps

A mixture of 24.18 g (0.06 mole) of 3-[(4-chlorophenyl)sulfonyl]-1-[(4-methylphenyl)sulfonyl]piperidine, 200 ml of 48% hydrobromic acid and 200 g (2.0 moles) of phenol was refluxed for 1.5 hr. The reaction mixture was cooled and poured into ice. The mixture was carefully made alkaline with 50% sodium hydroxide solution and extracted with diethyl ether. The ether layer was separated and held. The water layer was extracted with methylene chloride and separated, discarding the aqueous phase. The methylene chloride extract was evaporated on a rotary evaporator to give an oil which was combined with the ether layer. The new ether solution was back-extracted with 10% sodium hydroxide solution and the water layer discarded. The ether layer was next extracted with 1N sulfuric acid and the ether layer discarded. The acidic aqueous phase was made alkaline and extracted with methylene chloride. The methylene chloride layer was separated, dried and filtered, and the solvent was removed in vacuo to give a light yellow oil, the free base of the title compound. The free base was dissolved in methanol and an equimolar amount of fumaric acid in methanol was added. Addition of diethyl ether gave crystalline fumarate salt. The yield of white salt after drying over night at 100° C. in vacuo was 11.18 g (49.6%), m.p. 186°-187° C.

Provenance & Evidence