Toluene → Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Into 5 g (57 mmol) morpholine dissolved in 15 ml toluene, 4.6 ml (69 mmol) of 2-chlorohydrin was added dropwise. The mixture was heated to the reflux temperature and reacted for 5 h. After cooling, 20 ml of 5% NaOH solution was added to wash the reaction mixture. The organic layer obtained was washed with a saturated saline solution and dried over anhydrous sodium sulfate, then filtrated. Into the filtrate cooled in an ice bath, 8.3 ml (114 mmol) of thionyl chloride was added dropwise. After reacting for 12 h at room temperature, the reaction mixture was concentrated to dry in reduced pressure. The residue was recrystallized with ethyl acetate to obtain 5.9 g white solid with the yield of 55%. m.p. 182-184° C.

1. temperatureThe mixture was heated to the reflux temperature
2. customreacted for 5 h
3. temperatureAfter cooling
4. washto wash the reaction mixture
5. customThe organic layer obtained
6. washwas washed with a saturated saline solution
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltrated
9. temperatureInto the filtrate cooled in an ice bath
10. concentrationthe reaction mixture was concentrated
11. customto dry in reduced pressure
12. customThe residue was recrystallized with ethyl acetate

ORD record

ord-ecabaeed671e4adb8a76c40c4ee22ee2

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08664238B2