Dimethylformamide → 1-(4-Methyl-2-nitrophenyl)piperidine

Temperature

100 °C

Piperidine (660 μl, 6.66 mmol, commercially available product) was added at room temperature to an N,N-dimethylformamide (DMF; 1 ml) solution of 4-chloro-3-nitrotoluene (358 mg, 2.08 mmol, commercially available product). The resulting mixture was stirred at 100° C. for 17 hours. The mixture was cooled to room temperature, and then water was added thereto. The resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (50 g, hexane/ethyl acetate=50/1). Thus, 1-(4-methyl-2-nitrophenyl)piperidine (212 mg, 46.2%) was yielded as a colorless oily material. TLC Rf 0.54 (hexane/ethyl acetate=10/1).

1. temperatureThe mixture was cooled to room temperature
2. extractionThe resulting mixture was extracted three times with ethyl acetate
3. washThe obtained organic layer was washed with a saturated sodium chloride solution
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (50 g, hexane/ethyl acetate=50/1)

ORD record

ord-9d240ff4892d4d408335523ead24e3c3

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08816089B2