Dimethylformamide → 1-Methyl-4-(3-nitrophenyl)piperazine

Temperature

110 °C

A mixture of 1-fluoro-3-nitrobenzene (282 mg, 2.00 mmol), 1-methylpiperazine (401 mg, 4.00 mmol), potassium carbonate (276 mg, 2.00 mmol), and DMF (3 mL) was stirred and heated at 110° C. for 24 h. After cooling to rt, the mixture was poured into brine (10 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were extracted with aqueous HCl (1 N, 2×20 mL). The acidic extracts were basified by aqueous NaOH until pH>10. The basified aqueous solution was extracted with EtOAc (2×30 mL). The extracts were then washed with H2O (3×20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo to give the title compound as yellow oil. 1H NMR (CD3OD, 400 MHz): δ=2.22 (s, 3H), 2.48 (t, 4H, J=5.0 Hz), 3.16 (t, 4H, J=5.2 Hz), 7.16-7.18 (m, 1H), 7.27 (t, 1H, J=8.2 Hz), 7.46-7.49 (m, 1H), 7.57 (t, 1H, J=2.2 Hz). MS (ES+): m/z 222.26 (100) [MH+]. HPLC: tR=1.55 min (ZQ2000, polar—5 min).

1. temperatureAfter cooling to rt
2. extractionextracted with EtOAc (3×10 mL)
3. extractionThe combined organic extracts were extracted with aqueous HCl (1 N, 2×20 mL)
4. extractionThe basified aqueous solution was extracted with EtOAc (2×30 mL)
5. washThe extracts were then washed with H2O (3×20 mL) and brine (20 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-8fb3ba6f1106475a9d8e8a398a9aeb5a

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465726B2