Dichloromethane → HCID 22676671, compound

Temperature

0 °C

To the mixture of 1-(trifluoroacetyl)-4-benzylpiperidine (29.2 g, 108 mmol) and methylene chloride (10 ml) was dropwise added chlorosulfonic acid (36 ml, 539 mmol) at −10° C. for an hour. The mixture was stirred at 0° C. for an hour and then stirred at room temperature for an hour. The reaction mixture was poured into ice-cooled water (500 ml) and extracted with methylene chloride (200 ml×2). The extract was washed with an aqueous solution of 5% sodium bicarbonate (500 ml) and saturated brine (500 ml) successively. The organic phase was dried over magnesium sulfate (anhydrous), then concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel 100 g, ethyl acetate/hexane=1/20→1/5) to give the title compound as a colorless powdery crystal (16.5 g, 41%).

1. customat −10° C.
2. customfor an hour
3. stirringstirred at room temperature for an hour
4. additionThe reaction mixture was poured into ice-
5. extractionextracted with methylene chloride (200 ml×2)
6. washThe extract was washed with an aqueous solution of 5% sodium bicarbonate (500 ml) and saturated brine (500 ml) successively
7. dry with materialThe organic phase was dried over magnesium sulfate (anhydrous)
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by flash column chromatography (silica gel 100 g, ethyl acetate/hexane=1/20→1/5)

ORD record

ord-e6674d20524c4cbb8a87b964372fe417

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06787650B1