Diethyl Ether → Ethyl 2-(morpholin-3-yl)acetate

Temperature

16 °C

N-chloromorpholine (24 g) in diethyl ether (20 ml) was added drop-wise over 2.5 h to a vigorously stirred solution of potassium hydroxide (22.1 g, 0.37 mol) in ethanol (130 ml) at 90° C. Heating was continued at 80° C. for 2 h. After standing at room temperature for 48 h the mixture was filtered to remove the inorganics and the solvent removed from the filtrate in vacuo. The residue was partitioned between diethyl ether and brine, dried (Na2SO4) and the solvent removed in vacuo. The resulting brown oil was dissolved in acetonitrile (100 ml). Triethylamine (25 ml) and monoethyl malonate (25 g) were added and the mixture heated at 16° C. for 16 h. The volatiles were removed in vacuo and the residue partitioned between saturated aqueous potassium carbonate and diethyl ether. The organic phase was dried (Na2SO4) and the solvent removed in vacuo to afford the title compound as a brown oil (3.5 g).

1. temperatureHeating
2. waitAfter standing at room temperature for 48 h
3. filtrationthe mixture was filtered
4. customto remove the inorganics
5. customthe solvent removed from the filtrate in vacuo
6. customThe residue was partitioned between diethyl ether and brine
7. dry with materialdried (Na2SO4)
8. customthe solvent removed in vacuo
9. dissolutionThe resulting brown oil was dissolved in acetonitrile (100 ml)
10. additionTriethylamine (25 ml) and monoethyl malonate (25 g) were added
11. customThe volatiles were removed in vacuo
12. customthe residue partitioned between saturated aqueous potassium carbonate and diethyl ether
13. dry with materialThe organic phase was dried (Na2SO4)
14. customthe solvent removed in vacuo

ORD record

ord-83dfe76aa1c548ecb1e28bc666850a23

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470710B2