Piperidine → HCID 66586828, compound

Temperature

75 °C

Into a 1000-mL round-bottom flask, was placed a solution of 2-bromo-4-fluoro-1-nitrobenzene (30 g, 137.61 mmol, 1.00 equiv) in N,N-dimethylformamide (450 mL), piperidine (13.974 g, 162.68 mmol, 1.20 equiv), and potassium carbonate (56.718 g, 411.00 mmol, 2.99 equiv). The resulting solution was stirred overnight at 75° C. in an oil bath. The solids were filtered out. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 300 mL of dichloromethane. The resulting mixture was washed with 2×100 mL of water and 2×100 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:50). This resulted in 19 g (49%) of 1-(3-bromo-4-nitrophenyl)piperidine as a yellow solid.

1. customInto a 1000-mL round-bottom flask, was placed
2. filtrationThe solids were filtered out
3. concentrationThe resulting mixture was concentrated under vacuum
4. additionThe resulting solution was diluted with 300 mL of dichloromethane
5. washThe resulting mixture was washed with 2×100 mL of water and 2×100 mL of brine
6. dry with materialThe mixture was dried over anhydrous sodium sulfate
7. concentrationconcentrated under vacuum
8. washeluted with ethyl acetate/petroleum ether (1:50)
9. customThis resulted in 19 g (49%) of 1-(3-bromo-4-nitrophenyl)piperidine as a yellow solid

ORD record

ord-cbb92af5d3434a1eb3208bf4d3084570

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916569B2