1-(4-Nitrophenyl)piperazine → N,N-Dimethyl-4-(4-nitrophenyl)-1-piperazinepropanamine

Temperature

80 °C

Prepared according to a slightly modified procedure from U.S. Pat. No. 3,331,845. A mixture of 4-nitrophenylpiperazine (2.1 g, 10 mmol), sodium hydrogen carbonate (2.5 g, 30 mmol), N,N-dimethyl-N-(3-chloropropyl)amine hydrochloride (1.9 g, 12 mmol) in isopropanol (80 mL) was heated at 80° C. for 18 h. The mixture was then allowed to cool, the solid filtered off and the solvent removed under reduced pressure. Ethyl acetate (ca. 200 mL) was added and the residue was washed with saturated brine twice (50 mL each time). The organic layer was dried over sodium sulphate and the solvent evaporated under reduced pressure. The crude compound was purified by column, eluting with dichloromethane/methanol 9/1 (containing 1% N,N-dimethylethylamine) to give the title compound as a yellow solid. 1H NMR (CDCl3, 400 MHz): 1.6 (2H, m); 2.15 (6H, s); 2.25 (2H, m); 2.35 (2H, m); 2.5-2.55 (4H, m); 3.35-3.4 (4H, m); 6.75 (2H, d, J 8 Hz); 8.05 (2H, d, J 8 Hz) MS: 293, 248.

1. customPrepared
2. temperatureto cool
3. filtrationthe solid filtered off
4. customthe solvent removed under reduced pressure
5. additionEthyl acetate (ca. 200 mL) was added
6. washthe residue was washed with saturated brine twice (50 mL each time)
7. dry with materialThe organic layer was dried over sodium sulphate
8. customthe solvent evaporated under reduced pressure
9. customThe crude compound was purified by column
10. washeluting with dichloromethane/methanol 9/1 (containing 1% N,N-dimethylethylamine)

ORD record

ord-4488607be7d44888a91e9cb17467f0a7

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07442698B2