反应详情

Morpholine (0.13 mL, 1.5 mmol) was added to a suspension of nitroindanone (177 mg, 1.00 mmol) in 10 mL of toluene. The mixture was heated to reflux with stirring. A dark solution was obtained, and water was seen collecting in the condenser. After 3 h the solution was cooled. An aliquot was evaporated to dryness and the enamine was verified by 1H NMR. A dark solid separated from the solution on cooling. The bulk reaction mixture was evaporated to remove most of the solvent. 5 mL of methanol was added, which did not dissolve solid residue. 5 mL CH2Cl2 was added, which did dissolve most of the material. NaBH3CN (62.8 mg, 1.00 mmol) was added, followed by HOAc (1.00 mL). Stirring was continued overnight. Evaporated the solvent to dryness and partitioned the resulting residue between Na2CO3 and CH2Cl2. The aqueous phase was extracted with more CH2Cl2. The combined organic layers were dried over MgSO4 and evaporated. The residue was purified by column chromatography, CH2Cl2AMeOH gradient 1-10%, isolating 215 mg of 4-(5-nitro-indan-2-yl)-morpholine as a tan crystalline solid.

1. temperatureThe mixture was heated
2. temperatureto reflux
3. customA dark solution was obtained
4. customwater was seen collecting in the condenser
5. temperatureAfter 3 h the solution was cooled
6. customAn aliquot was evaporated to dryness
7. customA dark solid separated from the solution
8. temperatureon cooling
9. customThe bulk reaction mixture
10. customwas evaporated
11. customto remove most of the solvent
12. addition5 mL of methanol was added
13. dissolutionwhich did not dissolve solid residue
14. addition5 mL CH2Cl2 was added
15. dissolutionwhich did dissolve most of the material
16. stirringStirring
17. customEvaporated the solvent to dryness
18. custompartitioned the resulting residue between Na2CO3 and CH2Cl2
19. extractionThe aqueous phase was extracted with more CH2Cl2
20. dry with materialThe combined organic layers were dried over MgSO4
21. customevaporated
22. customThe residue was purified by column chromatography, CH2Cl2AMeOH gradient 1-10%