Benzaldehyde → HCID 21957880, compound

To a solution of benzaldehyde (10 mL) in toluene (200 mL) were added, under ice-cooling, 4-octylaniline (22.5 mL) and molecular sieves 4A (20 g), and the mixture was stirred overnight at room temperature. The molecular sieves 4A was filtered off from the reaction mixture and the obtained filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (200 mL) and sodium borohydride (2.3 g) was added under ice-cooling. The mixture was stirred at room temperature for 5 hr. Methanol was evaporated and water was added to the residue. The mixture was extracted with chloroform and the organic layer was washed with saturated brine, dried and concentrated under reduced pressure to give benzyl(4-octylphenyl)amine (29 g).

1. temperaturecooling
2. filtrationThe molecular sieves 4A was filtered off from the reaction mixture
3. concentrationthe obtained filtrate was concentrated under reduced pressure
4. dissolutionThe residue was dissolved in methanol (200 mL)
5. additionsodium borohydride (2.3 g) was added under ice-
6. temperaturecooling
7. customMethanol was evaporated
8. additionwater was added to the residue
9. extractionThe mixture was extracted with chloroform
10. washthe organic layer was washed with saturated brine
11. customdried
12. concentrationconcentrated under reduced pressure

ORD record

ord-ad9828f1c0864e9aa0b8e6045707c453

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105567B2