4-Nitrobenzaldehyde → HCID 18472483, compound

In 1,2-dichloroethane (75 ml) were suspended p-nitrobenzaldehyde (5 g) and 2-amino-1,3-propanediol (3.0 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 3.5 hours. To the mixture were added, under ice-cooling, 37% formalin (3 ml) and triacetoxy sodium boron hydride (9.8 g), and the mixture was stirred, under nitrogen atmosphere, at room temperature overnight. To the mixture was added water, and the mixture was concentrated. The residue was neutralized with sodium hydroxide solution, saturated with sodium hydrochloride and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified with silica gel column (ethyl acetate) to give 2-(N-methyl-N-(4-nitro-benzyl)amino)-1,3-propanediol (3.0 g) as pale yellow crystals.

1. additionto the mixture was added, under ice-
2. temperaturecooling
3. additionTo the mixture were added, under ice-
4. temperaturecooling
5. concentrationthe mixture was concentrated
6. extractionextracted with ethyl acetate
7. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
8. customthe solvent was evaporated under reduced pressure
9. customThe residue was purified with silica gel column (ethyl acetate)

ORD record

ord-1669f58f12264456ac4ac2883e3b0143

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06413947B1