4-Nitrobenzaldehyde → N-(3-ethoxypropyl)-N-methyl-4-nitrobenzylamine

In 1,2-dichloroethane (50 ml) were dissolved p-nitrobenzaldehyde (5 g) and 3-ethoxypropylamine (3.75 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 overnight, and to the mixture were added, under ice-cooling, 37% formalin (3.5 ml) and triacetoxy sodium boro hydride (9.8 g). Under nitrogen atmosphere, the mixture was stirred at room temperature for 8 hours, and the solvent was evaporated. The residue was neutralized with 1N sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and subjected to back extraction with 1N hydrochloric acid. The mixture was washed with ethyl acetate, neutralized with 1N sodium hydroxide 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 to give N-(3-ethoxypropyl)-N-methyl-4-nitrobenzylamine (6.6 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 for 8 hours
6. customthe solvent was evaporated
7. extractionthe mixture was extracted with ethyl acetate
8. washThe organic layer was washed with water
9. extractionextraction with 1N hydrochloric acid
10. washThe mixture was washed with ethyl acetate
11. extractionextracted with ethyl acetate
12. washThe organic layer was washed with water and saturated brine
13. dry with materialdried with anhydrous magnesium sulfate
14. customUnder reduced pressure, the solvent was evaporated

ORD record

ord-4a52975d4e5444bab6777ad5c9d2bc1c

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06166006