反应详情

温度

80 °C

2-Nitro-5-phenoxy-benzaldehyde (2.14 g, 0.00882 mol) was added to a solution of 3-amino-N-cyclohexyl-N-methyl-propionamide (1.5 g, 0.00882 mol) in 100 mL of 1,2-dichloroethane, and the mixture was stirred at 80° C. for 1 hour. Sodium triacetoxyborohydride (2.87 g, 0.00882 mol) was added at room temperature, and the reaction mixture was stirred for 15 h. Additional sodium triacetoxyborohydride (1 g) was added, and the reaction mixture was stirred another 20 h at room temperature. To the reaction mixture was added 10% aqueous NaOH solution (50 mL), and the mixture was extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered, and concentrated to yield a residue which was purified by column chromatography over silica gel using 97:3 CH2Cl2:MeOH as the eluent. The product containing fractions were combined and evaporated to yield a side product (MW 638). The residue was further purified by column chromatography over silica gel using 97:3 CH2Cl2:MeOH. The product containing fractions were combined and evaporated to yield a residue. The fractions containing impure product were combined and evaporated to yield a second residue, which was purified by silica gel chromatography to yield additional desired product.

1. stirringthe reaction mixture was stirred for 15 h
2. stirringthe reaction mixture was stirred another 20 h at room temperature
3. extractionthe mixture was extracted with CH2Cl2
4. customThe organic layer was separated
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customto yield a residue which
9. customwas purified by column chromatography over silica gel using 97:3 CH2Cl2
10. additionThe product containing fractions
11. customevaporated
12. customto yield a side product (MW 638)
13. customThe residue was further purified by column chromatography over silica gel using 97:3 CH2Cl2
14. additionThe product containing fractions
15. customevaporated
16. customto yield a residue
17. additionThe fractions containing impure product
18. customevaporated
19. customto yield a second residue, which
20. customwas purified by silica gel chromatography