Carbon Tetrachloride → HCID 12955538, compound

Temperature

0 °C

To a flask was added 5.0 g. (0.03 mole) of 4-(2-hydroxyethyl)-2,6-dimethylmorpholine in 50 ml. of carbon tetrachloride followed by 10.2 g. (0.04 mole) of triphenylphosphine. The mixture was stirred at reflux for three hours, then the reaction was cooled to 0° C., the triphenylphosphine oxide was filtered and the solvent stripped. The residue was dissolved in 10% aqueous hydrochloric acid and the by-products were extracted into ethyl acetate. The acid layer was then basified with ammonium hydroxide and extracted into ethyl acetate. The ethyl acetate solution was dried with magnesium sulfate, filtered, and concentrated. The crude product was further purified by flash chromatography to give 2.31 g. (43% yield) of 4-(2-chloroethyl)-2,6-dimethylmorpholine as a colorless liquid.

1. additionTo a flask was added 5.0 g
2. temperatureat reflux for three hours
3. filtrationthe triphenylphosphine oxide was filtered
4. dissolutionThe residue was dissolved in 10% aqueous hydrochloric acid
5. extractionthe by-products were extracted into ethyl acetate
6. extractionextracted into ethyl acetate
7. dry with materialThe ethyl acetate solution was dried with magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was further purified by flash chromatography
11. customto give 2.31 g

ORD record

ord-3c01799ec72a4355b3297254bf6f3ea4

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05240925