Morpholine → 1-(2-Chloro-4-(morpholinomethyl)phenyl)ethanone

Temperatur

40 °C

A mixture of 1-(4-(bromomethyl)-2-chlorophenyl)ethanone (1.65 g, 6.65 mmol) (preparation 16) and acetonitrile (25 ml) was prepared at room temperature and stirred under nitrogen. Potassium carbonate (1.10 g 7.98 mmol) was then added followed by morpholine (0.695 ml, 7.98 mmol) and the mixture stirred at room temperature. After 2 h, TLC indicated the presence of both product and starting material. The mixture was then heated under nitrogen to 40° C. for 16 h, then allowed to cool to room temperature, filtered to remove excess carbonate and filtrate concentrated under reduced pressure. The mixture was then diluted in DCM (30 ml), washed with water (2×10 ml), filtered through a phase separator and the filtrate concentrated under reduced pressure. The crude mixture was purified by column chromatography (40-100% EtOAc/hexane) to afford 1-(2-chloro-4-(morpholinomethyl)phenyl)ethanone as a yellow oil (1.08 g, 4.25 mmol, 64%).

1. customwas prepared at room temperature
2. stirringthe mixture stirred at room temperature
3. temperatureto cool to room temperature
4. filtrationfiltered
5. customto remove excess carbonate and filtrate
6. concentrationconcentrated under reduced pressure
7. additionThe mixture was then diluted in DCM (30 ml)
8. washwashed with water (2×10 ml)
9. filtrationfiltered through a phase separator
10. concentrationthe filtrate concentrated under reduced pressure
11. customThe crude mixture was purified by column chromatography (40-100% EtOAc/hexane)

ORD-Eintrag

ord-8b9f61eaa1fd4e3cbc892b9b51255e6f

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09115088B2