Ethanolamine → 2-(4-Chloro-benzylamino)-ethanol

Temperature

0 °C

To a solution of ethanolamine (1.2 eq.) in either MeOH or THF were added NaHCO3 (1.5 eq.) and 4-chlorobenzaldehyde (1 eq.). The reaction was refluxed for 4 h, then cooled to 0° C. NaBH4 (1.2 eq.) was added portionwise. The reaction was stirred for 1 h at 0° C., then 15 h at 20° C. The crude was concentrated under reduced pressure then partitioned between water and DCM. The aqueous layer was then extracted twice with DCM. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with DCM/MeOH: 1/0 to 95/5) to afford 2-(4-chloro-benzylamino)-ethanol.

1. temperatureThe reaction was refluxed for 4 h
2. custom15 h
3. customat 20° C
4. concentrationThe crude was concentrated under reduced pressure
5. customthen partitioned between water and DCM
6. extractionThe aqueous layer was then extracted twice with DCM
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe crude was purified by chromatography on silica gel (elution with DCM/MeOH: 1/0 to 95/5)

ORD record

ord-bc4addb90c7f49ce91f792e1b8b06d90

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759334B2