Hydrochloric Acid → 4-(3-Chloropropyl)morpholinium chloride

5 ml acetonitrile, 2.3 ml (23 mmol) of 1-bromo-3-chloropropane and 1 ml (11.5 mmol) of morpholine were added successively into a reaction flask. The mixture was stirred for 1 h, and 0.5 ml of 5% NaOH solution was added. After stirring at room temperature for 12 h, 3 ml concentrated hydrochloric acid and 10 ml water were added into the mixture. The lower layer was discarded, and the upper layer was alkalified with 5% NaOH and extracted with ethyl acetate. The organic layer was washed with a saturated saline solution and dried over anhydrous sodium sulfate, then filtrated. The filtrate was concentrated to dry in a reduced pressure, and a small amount of ethanol/NaOH solution was added dropwise into the residue. The mixture was shaken and placed in a refrigerator for standing, then concentrated to dry in a reduced pressure to obtain 1.4 g white solid with the yield of 60%. m.p. 168-170° C.

1. stirringAfter stirring at room temperature for 12 h
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with a saturated saline solution
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltrated
6. concentrationThe filtrate was concentrated
7. customto dry in a reduced pressure
8. additiona small amount of ethanol/NaOH solution was added dropwise into the residue
9. stirringThe mixture was shaken
10. concentrationconcentrated
11. customto dry in a reduced pressure

ORD record

ord-798bc0cd7d9b4e189900c4f47b23d886

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08664238B2