N,N'-Dimethylethylenediamine → (R)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanone

Participants

Reaction Steps

To a mixture of [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone (848 mg) described in Preparation Example 113, (R)-3-methylisothiazolidine 1,1-dioxide (272 mg) described in Preparation Example 2, potassium carbonate (555 mg) and copper(I) iodide (192 mg) were added toluene (4 mL) and N,N′-dimethylethylenediamine (0.20 mL), and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled, water was added, the mixture was extracted with chloroform, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give (R)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][4-(3-methyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]methanone. The obtained (R)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][4-(3-methyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]methanone (453 mg) was dissolved in ethyl acetate, 4N hydrogen chloride/ethyl acetate (0.26 mL) was added, and the precipitate was collected by filtration to give the title compound (372 mg).

Provenance & Evidence