Hydrochloric Acid → HCID 18354551, compound

Participants

Reaction Steps

A solution of 1-chloroethylchloroformate (0.12 ml;1.11 mmol) and 5,8-dimethoxy-2-[4-methoxy-3-(4-methyl-1-piperazinyl)benzenesulfonyl]-1,2,3,4-tetrahydroisoquinoline (E21) (111 mg;0.223 mmol) in 1,2-dichloroethane (3 ml) was refluxed for 0.75 h, cooled, diluted with diisopropylethylamine (0.19 ml;1.11 mmol) and refluxed for a further 2.5 hrs. The solution was concentrated to a residue which was re-dissolved in methanol, refluxed for 1 hr and then stirred at room temperature for 24 h. The mixture was concentrated, and the residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was dried, concentrated to a residue and purified by column chromatography on silica gel using a methanol/dichloromethane solvent gradient. The title compound was prepared by dissolving the pure free base material from chromatography in acetone/dichloromethane and acidifying with 1M ethereal HCl (53 mg, 49%). MH+456/458.

Provenance & Evidence