Nitrogen → HCID 23593636, compound

Participants

Reaction Steps

3-[2-(2,4-Dichlorophenylsulfanyl)phenylamino]piperidine-1-carboxylic acid tert-butyl ester (8.4 g, 18.5 mmol) was dissolved in DMF (120 mL) and vigorously degassed with N2 for 20 min. Cesium carbonate (27.2 g, 83.5 mmol), copper(I) iodide (5.28 g, 27.8 mmol), and copper powder (8.4 g, 1321 mmol) were added to the solution. The suspension was stirred vigorously and heated to 155–156° C. for 12 hours (N2 was continuously bubbled through the mixture). The mixture was cooled to room temperature and diluted with ethyl acetate. The solids were removed by vacuum filtration and were rinsed with ethyl acetate. The filtrate was concentrated under vacuum to remove 90% of the volatiles. The residue was purified by SiO2 chromatography to provide 3-(2-chlorophenothiazin-10-yl) piperidine-1-carboxylic acid tert-butyl ester (4.1 g, 53%) as a white solid.

Provenance & Evidence