반응 #2396365
ord-cf10606eff4e4f6aaf979809a3c27649
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후처리
- 1workup.STIRRINGAfter stirring for 1 hour
- 2온도to warm to ambient temperature
- 3workup.STIRRINGstirred for 17 hours
- 4기타After evaporation of methylene chloride
- 5workup.DISSOLUTIONthe residue was dissolved in water (50 ml)
- 6기타The precipitate was removed by filtration
- 7추출the filtrate was extracted with ethyl acetate (300 ml)
- 8세척The extract was washed with water
- 9건조dried over magnesium sulfate
- 10기타evaporated in vacuo
- 11기타The residue was chromatographed on silica gel (40 g)
- 12workup.ADDITIONThe fractions containing the desired compound
- 13농축concentrated under reduced pressure
- 14기타The residue was recrystallized from ethyl acetate
실험 절차
To a solution of trichloromethyl chloroformate (2.76 ml) in methylene chloride (200 ml) was added a solution of 3-aminopyridine (2.165 g) in methylene chloride (50 ml) and stirred for 2 hours at -50° C. The mixture was added to a mixture of N-amino-1,2,3,6-tetrahydropyridine hydrochloride (3.096 g) and triethylamine (2.327 g) in methylene chloride (100 ml) and the resultant mixture was stirred at the same temperature. After stirring for 1 hour, the reaction mixture was allowed to warm to ambient temperature and stirred for 17 hours. After evaporation of methylene chloride, the residue was dissolved in water (50 ml) and the resultant aqueous solution was adjusted to pH 8.0-8.5 with sodium bicarbonate. The precipitate was removed by filtration and the filtrate was extracted with ethyl acetate (300 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (40 g) using chloroform. The fractions containing the desired compound were combined and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give N-[(3-pyridylcarbamoyl)amino]-1,2,3,6-tetrahydropyridine (1.62 g).