Morpholine → 4-(2,6-dichloro-pyridin-4-yl)-morpholine

Temperature

0 °C

A mixture of morpholine (0.604 g, 6.04 mmol) in dry DMSO and NaH (0.251 g, 6.6 mmol) was stirred for 30 minutes at 0° C., after which time 2,4,6-trichloropyridine (1.0 g, 5.50 mmol) was added. This reaction mixture was stirred at room temperature for 4 hours, after which time ice cold water was added to quench the reaction (100 mL). The reaction mixture was then extracted with ethyl acetate, and the extract was washed with 3-4 times water. The organic layer was dried over sodium sulphate and concentrated under vacuum. The residue was purified by column chromatography over 100-200 mesh silica gel. Elution of the column with 20% acetone in hexanes gave the pure product as a colorless solid (0.565 g, yield 44%).

1. stirringThis reaction mixture was stirred at room temperature for 4 hours
2. additionafter which time ice cold water was added
3. customto quench
4. customthe reaction (100 mL)
5. extractionThe reaction mixture was then extracted with ethyl acetate
6. washthe extract was washed with 3-4 times water
7. dry with materialThe organic layer was dried over sodium sulphate
8. concentrationconcentrated under vacuum
9. customThe residue was purified by column chromatography over 100-200 mesh silica gel
10. washElution of the column with 20% acetone in hexanes

ORD record

ord-5686a5a9c4d546dfa2b416e070d0869e

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622486B2