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

Temperature

60 °C

Substituted benzaldehyde (0.01 mol), such as 4-chloro benzaldehyde (1.4 g), was dissolved in dry ethanol (30 mL) and ethanolamine (0.61 g, 0.01 mol) was added. The reaction mixture was stirred overnight at 60° C. The ethanol was evaporated under reduced pressure to give a colorless oil. The oil was then dissolved in dry methanol (30 mL) and cooled in ice. Sodium borohydride (NaBH4, 0.57 g, 0.015 mol) was added slowly in portions, and the resulting solution was left overnight at room temperature. The solvent was evaporated in vacuo, and the residue was dissolved in water, and extracted with CH2Cl2 (3×20 mL). The organic layers were combined and dried with Na2SO4, filtered and evaporated in vacuo to give colorless oily residue, which was purified by column chromatography (silica gel CH2Cl2:MeOH=9:1) to give 2-(4-chlorobenzylamino)-ethanol (II-1, 1.83 g, 99%).

1. customThe ethanol was evaporated under reduced pressure
2. customto give a colorless oil
3. temperaturecooled in ice
4. waitthe resulting solution was left overnight at room temperature
5. customThe solvent was evaporated in vacuo
6. dissolutionthe residue was dissolved in water
7. extractionextracted with CH2Cl2 (3×20 mL)
8. dry with materialdried with Na2SO4
9. filtrationfiltered
10. customevaporated in vacuo
11. customto give colorless oily residue, which
12. customwas purified by column chromatography (silica gel CH2Cl2:MeOH=9:1)

ORD record

ord-198e63da98524556a4094c51413e2b23

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994326B2