反应详情

To a solution of 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (1 g) in formic acid (14 ml), zinc powder (1 g) was added and the reaction mixture was stirred at room temperature for 3 hours. The insoluble solid was removed by filtration. The filtrate was evaporated to dryness and the residue was dissolved in water (30 ml). The solution was adjusted to pH 7.0 by 1N aqueous sodium hydroxide. The precipitates were extracted with chloroform (although the solution was converted into an emulsion at this extracting step, the operation was facilitated by using a filter aid such as "Avicel"). The extract was dried over anhydrous magnesium sulfate and chloroform was removed under reduced pressure. The crude product was purified by the preparative thin layer chromatography [Merck TLC plate, silica gel 60F254 (particles average porous diameter 60A, Fluorescent substance Zn2SiO4 /Mn), 20×20 cm, t=1 mm, chloroform/methanol=20/1] to give 20 mg of 5-methyl-6-(4-pyridinyl)- 2H-1,4thiazin-3(4H)-one. The physical properties were as described above. The aqueous layer left after the chloroform extraction was adjusted to pH 12.5 by 1N aqueous sodium hydroxide and extracted with chloroform (50 ml×3 times). The extract was dried over anhydrous magnesium sulfate and chloroform was removed under reduced pressure. The residual solid was washed with ether and collected by filtration to give 5-methyl-6-(4-piperidinyl)-2H-1,4-thiazin-3(4H)-one (200 mg) as a light yellow powder.

1. customThe insoluble solid was removed by filtration
2. customThe filtrate was evaporated to dryness
3. dissolutionthe residue was dissolved in water (30 ml)
4. extractionThe precipitates were extracted with chloroform (although the solution
5. dry with materialThe extract was dried over anhydrous magnesium sulfate and chloroform
6. customwas removed under reduced pressure
7. customThe crude product was purified by the preparative thin layer chromatography [Merck TLC plate, silica gel 60F254 (particles average porous diameter 60A, Fluorescent substance Zn2SiO4 /Mn), 20×20 cm, t=1 mm, chloroform/methanol=20/1]