Bromine → HCID 21097317, compound

Temperature

60 °C

4-(1-Methyl-1H-imidazol-2-yl)-morpholine (Nagarajan, K. et al. Indian J. Chem. Sect. B, 21, 10, 1982, 949–952) (1.02 g, 6.08 mmol) was dissolved in 35 mL of 1,4-dioxane under and N2 atmosphere. The mixture was heated to 60° C. and a solution of 0.34 mL (6.4 mmol) of Br2 in 10 mL of dichloroethane was added slowly. The mixture was heated for 1 h, then cooled. The mixture was concentrated and the residue was partitioned between 6.5 mL of 1 N NaOH and 25 mL of EtOAc. The NaOH solution was extracted twice more with EtOAc, and the extracts were washed with NaHCO3 and brine, dried with Na2SO4, filtered, concentrated, and chromatographed (0–4% MeOH (0.5% NH4OH) in CH2Cl2) to provide 464 mg of 4-(5-bromo-1-methyl-1H-imidazol-2-yl)-morpholine.

1. temperatureThe mixture was heated for 1 h
2. temperaturecooled
3. concentrationThe mixture was concentrated
4. customthe residue was partitioned between 6.5 mL of 1 N NaOH and 25 mL of EtOAc
5. extractionThe NaOH solution was extracted twice more with EtOAc
6. washthe extracts were washed with NaHCO3 and brine
7. dry with materialdried with Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customchromatographed (0–4% MeOH (0.5% NH4OH) in CH2Cl2)

ORD record

ord-964378c073bd452fa757c1ec58a8e689

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07214802B2