Water → N-Ethyl-4-chlorobenzylamine

Temperature

20 °C

To a solution of 4-chlorobenzaldehyde (1 eq.) in MeOH was added ethylamine 70% in water (10 eq.). The reaction was stirred for 15 h at 20° C. under argon then NaBH4 (2 eq.) was added. The reaction was stirred at 20° C. for 5 h. The reaction was quenched with water then acidified with aqueous HCl (2M). The aqueous layer was washed with EtOAc. The organic layer was discarded. Aqueous NaOH (2M) was then added to the aqueous layer until pH=10 and the crude was extracted twice with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to afford (4-chloro-benzyl)-ethyl-amine.

1. stirringThe reaction was stirred at 20° C. for 5 h
2. customThe reaction was quenched with water
3. washThe aqueous layer was washed with EtOAc
4. additionAqueous NaOH (2M) was then added to the aqueous layer until pH=10
5. extractionthe crude was extracted twice with EtOAc
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-9cbdd250aa5e45388d9c0e02b231ef54

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759334B2