1-(3-Nitrophenyl)piperazine synthesis
- Product Name:1-(3-Nitrophenyl)piperazine
- CAS Number:54054-85-2
- Molecular formula:C10H13N3O2
- Molecular Weight:207.23
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Yield: 72%
Reaction Conditions:
with potassium carbonate in dimethyl sulfoxide at 100; for 24 h;
Steps:
2-1; 3.1
A mixture of piperazine (12 g, 138 mmol), 1-fluoro-3-nitrobenzene (4 ml, 34 mmol) and potassium carbonate (9.60 g, 69 mmol) in DMSO (40 mL) is heated at 100°C for 24 h. The reaction is quenched with H2O (60 mL) and extracted with Et2O (3 x 20 mL). The organic layer is washed with brine (20 mL) and dried over Na2SO4 and concentrated in vacuo. The residue is chromatographied on silica gel eluting with CH2Cl2/ MeOH (94 / 6) to yield the title compound (5.15 g, 72%) as an orange solid. This solid was dissolved in CH2Cl2 and Boc2O (6 g, 130 mmol) was added. The mixture was stirred overnight. The solvent was evaporated and the residual solid was crystallized in heptane (6.80 g, 93%, mp 86°C). 1H NMR (200 MHz, CDCl3) δ 1.49 (s, 9 H), 3.22-3.27 (m, 4 H), 3.58-3.63 (m, 4 H), 7.16-7.71 (m, 4 H).
References:
INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM) EP1683790, 2006, A1 Location in patent:Page/Page column 7; 12
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