Chlorosulfonic acid → HCID 22676671, compound

Temperature

0 °C

A mixture of 1-(trifluoroacetyl)-4-benzylpiperidine (29.2 g, 108 mmol) and dichloromethane (10 ml) was added dropwise to chlorosulfonic acid (36 ml, 539 mmol) over period of 1 h at −10° C. The mixture was stirred at 0° C. for 1 h and then at room temperature for 1 h. The whole was poured into ice-water (500 ml). The mixture was extracted with dichloromethane (200 ml×2). The extracts were washed with 5% aqueous sodium bicarbonate (500 ml), saturated sodium chloride solution (500 ml) successively. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel 100 g, ethyl acetate/hexane=1/20 to 1/5) to obtain the title compound (16.5 g, 41%) as a colorless crystalline powder.

1. waitat room temperature for 1 h
2. extractionThe mixture was extracted with dichloromethane (200 ml×2)
3. washThe extracts were washed with 5% aqueous sodium bicarbonate (500 ml), saturated sodium chloride solution (500 ml) successively
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. concentrationconcentrated in vacuo
6. customThe residue was purified by flash column chromatography (silica gel 100 g, ethyl acetate/hexane=1/20 to 1/5)

ORD record

ord-74355547d2874b488d7c770ee7c91b8f

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06562978B1