Water → Tetrahydroquinoxaline bis(chloroacetamide)

Temperature

0 °C

To a 1 L three-necked round bottomed flask equipped with a magnetic stir bar, reflux condenser and addition funnel, was added chloroacetyl chloride (9.6 mL, 0.120 mol) and CHCl3 (100 mL). The addition funnel was charged with a solution of tetrahydroquinoxaline (8.0 g, 0.0596 mol) and triethylamine (20.8 mL) in CHCl3 (100 mL). The flask was chilled to 0° C., and the amine was slowly added to the acid chloride. After the addition was complete, the mixture was allowed to warm to ambient temperature and stir for 1 hour. The flask was then cooled to 0° C. and H2O (50 mL) was slowly added. The mixture was diluted with CHCl3 (250 mL) and the layers were separated. The organic layer was washed with H2O (50 mL), 0.05 N NaOH (2×50 mL), H2O (50 mL), 1 N HCl (3×50 mL) and H2O (2×50 mL), and was dried over anhydrous Na2SO4. The solution was filtered and concentrated to a brown solid. The solid was collected by filtration, washed with 2-propanol (2×30 mL) and diethylether (2×40 mL) and dried to yield the title product (4.41 g, 51.5%). 1H NMR (DMSO-d6): δ3.89 (s, 4 H), 4.01 (s, 4 H), 7.25 (s, 2 H), 7.65 (br s, 2 H).

1. customTo a 1 L three-necked round bottomed flask equipped with a magnetic stir bar
2. temperaturereflux
3. additioncondenser and addition funnel
4. additionAfter the addition
5. temperatureto warm to ambient temperature
6. temperatureThe flask was then cooled to 0° C.
7. customthe layers were separated
8. washThe organic layer was washed with H2O (50 mL), 0.05 N NaOH (2×50 mL), H2O (50 mL), 1 N HCl (3×50 mL) and H2O (2×50 mL)
9. dry with materialwas dried over anhydrous Na2SO4
10. filtrationThe solution was filtered
11. concentrationconcentrated to a brown solid
12. filtrationThe solid was collected by filtration
13. washwashed with 2-propanol (2×30 mL) and diethylether (2×40 mL)
14. customdried

ORD record

ord-82e1b2642b74419b97afa09fdbcd1fe5

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05972307