Triethylamine → N,N-dimethyl-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-4-amine

To 1-benzyl-N,N-dimethylpiperidin-4-amine dihydrochloride (6.7 g, 23 mmol) was added Pd/C (10%, 2.4 g) under argon. Methanol (100 ml) was added via syringe, and H2 gas was introduced and the mixture stirred vigorously under an atmosphere of H2. After 48 h, the mixture was flushed with nitrogen, filtered through celite and concentrated to afford a mixture of starting material and N,N-dimethylpiperidin-4-amine dihydrochloride as a white solid. This solid was treated with 1-Fluoro-2-nitro-4-trifluoromethyl-benzene (3.2 ml, 22.9 mmol), triethylamine (12.7 ml, 92 mmol), and 50 ml dry THF. The mixture was heated to 75° C. with a water-cooled reflux condenser for 12 h. The mixture was allowed to cool to ambient temperature, was filtered through a fritted funnel, and concentrated to an orange oil. The residue was purified by silica gel chromatography (MC/MeOH/conc. NH4OH) to give the desired product as an orange oil. MS (m/z): 318.1 (M+H)+. Calc'd for C14H18F3N3O2: 317.31.

1. additionH2 gas was introduced
2. customthe mixture was flushed with nitrogen
3. filtrationfiltered through celite
4. concentrationconcentrated
5. customto afford
6. temperaturecooled
7. temperaturereflux condenser for 12 h
8. filtrationwas filtered through a fritted funnel
9. concentrationconcentrated to an orange oil
10. customThe residue was purified by silica gel chromatography (MC/MeOH/conc. NH4OH)

ORD record

ord-394cd116af3b495585fc28497a42fcea

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07776869B2