4-Nitrobenzaldehyde → N-(2-methoxyethyl)-N-methyl-4-nitrobenzylamine

In 1,2-dichloroethane (50 ml) were dissolved p-nitrobenzaldehyde (5 g) and 2-methoxyethylamine (2.7 g), and to the mixture was added, under ice-cooling, triacetoxy sodium boro hydride (9.8 g). Under nitrogen atmosphere, the mixture was stirred at room temperature for 4 hours, and to the mixture were added, under ice-cooling, 37% formalin (3.8 ml) and triacetoxy sodium boro hydride (10 g). Under nitrogen atmosphere, the mixture was stirred at room temperature overnight, and the solvent was evaporated. The residue was neutralized with 1N sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate/hexane) to give N-(2-methoxyethyl)-N-methyl-4-nitrobenzylamine (5.9 g) as yellow oil.

1. additionto the mixture was added, under ice-
2. temperaturecooling
3. additionto the mixture were added, under ice-
4. temperaturecooling
5. stirringUnder nitrogen atmosphere, the mixture was stirred at room temperature overnight
6. customthe solvent was evaporated
7. extractionextracted with ethyl acetate
8. washThe organic layer was washed with water and saturated brine
9. dry with materialdried with anhydrous magnesium sulfate
10. customUnder reduced pressure, the solvent was evaporated
11. customthe residue was purified with silica gel column (ethyl acetate/hexane)

ORD record

ord-251b93829dc24e728b7801ec813f3813

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06172061B2