반응 #50924

반응 방정식

6-thiomorpholin-4-yl-4-o-tolyl-pyridin-3-ylamine

potassium carbonate

ethyl cloroformate

sodium bis(2-methoxyethoxy)aluminum hydride

sodium hydroxide

→

title compound

수율 92.0%

Methyl-(6-thiomorpholin-4-yl-4-o-tolyl-pyridin-3-yl)-amine

수율 92.0%

용매

tetrahydrofuran

toluene

반응 조건

후처리

1. 1
   기타evaporated
2. 2
   기타to remove tetrahydrofuran
3. 3
   추출The aqueous layer was extracted twice with 50-ml portions of dichloromethane
4. 4
   건조the organic layer was dried (sodium sulfate)
5. 5
   기타evaporated in vacuo
6. 6
   workup.DISSOLUTIONThe residual oil was dissolved in 30 ml tetrahydrofuran
7. 7
   workup.STIRRINGThe reaction mixture was stirred at 50° C. overnight
8. 8
   온도After cooling to 0° C.
9. 9
   기타Tetrahydrofuran was removed in vacuo and 10 ml of water
10. 10
    workup.ADDITIONwere added
11. 11
    추출The aqueous layer was extracted twice with 20-ml portions of dichloromethane
12. 12
    건조the combined organic layers were dried (sodium sulfate)
13. 13
    기타evaporated
14. 14
    기타purified by flash chromatography

실험 절차

To a solution of 2.46 g (8.6 mmol) 6-thiomorpholin-4-yl-4-o-tolyl-pyridin-3-ylamine in 38 ml tetrahydrofuran were added 2.38 g (17 mmol) potassium carbonate (dissolved in 25 ml water) and 1.03 g (9.5 mmol) ethyl cloroformate. The reaction mixture was stirred for 1 h at room temperature and evaporated to remove tetrahydrofuran. The aqueous layer was extracted twice with 50-ml portions of dichloromethane and the organic layer was dried (sodium sulfate) and evaporated in vacuo. The residual oil was dissolved in 30 ml tetrahydrofuran and 7.4 ml (2.6 mmol) 3.5 M sodium bis(2-methoxyethoxy)aluminum hydride solution in toluene were added within 30 min. The reaction mixture was stirred at 50° C. overnight. After cooling to 0° C., 7.5 ml 1 N sodium hydroxide solution were added dropwise. Tetrahydrofuran was removed in vacuo and 10 ml of water were added. The aqueous layer was extracted twice with 20-ml portions of dichloromethane and the combined organic layers were dried (sodium sulfate), evaporated and purified by flash chromatography to give 2.37 g (92%) of the title compound as a yellow solid.

출처