4-Nitrobenzaldehyde → HCID 18472591, compound

In 1,2-dichloroethane (50 ml) were dissolved p-nitrobenzaldehyde (5 g) and 3-methoxypropylamine (3.1 g), and to the mixture was added, under ice-cooling, triacetoxy sodium boron hydride (9.8 g). Under nitrogen atmosphere, the mixture was stirred at room temperature for 3 hours, and to the mixture were added, under ice-cooling, 37% formalin (3 ml) and triacetoxy sodium boron hydride (9.8 g). Under nitrogen atmosphere, the mixture was stirred at room temperature for 3 hours, and to the mixture was added water. The mixture was concentrated, neutralized with sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with water and subjected to back extraction with 1N hydrochloric acid. The aqueous layer was washed with ethyl acetate, 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 to give N-(3-methoxypropyl)-N-methyl-4-nitrobenzylamine (5.6 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 3 hours
6. concentrationThe mixture was concentrated
7. extractionextracted with ethyl acetate
8. washThe organic layer was washed with water
9. extractionextraction with 1N hydrochloric acid
10. washThe aqueous layer 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-7b7df84329fb46ffb1e18cef6ee01260

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06172061B2