Morpholine → 4-Morpholinecarbonyl chloride

Temperature

0 °C

Into a 500-mL round-bottom flask was placed ditrichloromethyl carbonate (10.2 g, 34.37 mmol, 1.50 equiv) and dichloromethane (100 mL). This was followed by the addition of morpholine (2 g, 22.96 mmol, 1.00 equiv) dropwise with stirring at 0° C. in 2 min. To this was added TEA (4.2 g, 41.51 mmol, 1.81 equiv) dropwise with stirring at 0° C. in 3 min. The resulting solution was stirred for 3 h at room temperature. The reaction was then washed by the addition of 100 mL of water. The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). Purification afforded 2.238 g (65%) of morpholine-4-carbonyl chloride as a light yellow oil.

1. customInto a 500-mL round-bottom flask was placed
2. stirringwith stirring at 0° C. in 3 min
3. stirringThe resulting solution was stirred for 3 h at room temperature
4. washThe reaction was then washed by the addition of 100 mL of water
5. dry with materialThe mixture was dried over anhydrous sodium sulfate
6. filtrationThe solids were filtered out
7. concentrationThe resulting mixture was concentrated under vacuum
8. customPurification

ORD record

ord-353ba017881546e48968e38728bed6ae

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969557B2