3-Phenylbenzaldehyde → 3-(Aminomethyl)biphenyl

Temperature

60 °C

To a solution of 3-biphenylcarboxaldehyde (0.011 eq.) in 30 mL of methanol was added 10 eq. of 7N NH3/MeOH and NaCNBH4 (2 eq.). A yellow gum precipitated from solution. The solution was then heated at 60° C. until gum dissolved and the solution was stirred at room temperature overnight. The reaction mixture was then concentrated and the resulting residue diluted with ice water and ethyl acetate. The organic layer was then washed with brine and extracted with 5N HCl. The pH of the aqueous layer was then adjusted to 12 and the aqueous layer was extracted with cold ethyl acetate. The organic layer was dried over Na2SO4, filtered and concentrated to give 3-(phenyl)benzyl amine as an oil.

1. customA yellow gum precipitated from solution
2. dissolutiondissolved
3. concentrationThe reaction mixture was then concentrated
4. additionthe resulting residue diluted with ice water and ethyl acetate
5. washThe organic layer was then washed with brine
6. extractionextracted with 5N HCl
7. extractionthe aqueous layer was extracted with cold ethyl acetate
8. dry with materialThe organic layer was dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-1a58d1e6758d41e7846c1d9159212b4f

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06849650B2