Buchwald–Hartwig amination: 4-Bromo-2-nitroanisole → 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanone
30% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 4-Bromo-2-nitroanisole | C₇H₆BrNO₃ | |
| Reactant | 1-Acetylpiperazine | C₆H₁₂N₂O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanone | C₁₃H₁₇N₃O₄ | 29.91% |
Conditions
- Temperature
- 100 °C
Yield
- 30% of 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanone.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
- 1-[4-(2-Methyl-3-nitrophenyl)piperazin-1-yl]ethanone98%
- cis-3,5-Dimethyl-1-[4-(methyloxy)-3-nitrophenyl]piperazine56%
- 1-[4-(5-Bromo-3-pyridinyl)piperazin-1-yl]ethanone32%
- 1-(7-(4-Methoxy-3-nitrophenyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl)ethanone0%
- 1-(7-(4-Methoxy-3-nitrophenyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl)ethanone0%
Procedure
Copied from the source record, unedited
4-bromo-1-methoxy-2-nitrobenzene (30 g, 129.29 mmol), 1-(piperazin-1-yl)ethanone (16.57 g, 129.29 mmol), cesium carbonate (84 g, 258.59 mmol),diacetoxypalladium (2.322 g, 10.34 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (8.98 g, 15.52 mmol) in dioxane (200 mL) were degazed with nitrogen and stirred at 100°C for 1 hour. The reaction mixture was allowed to cool to room temperature, water (1000mL) was added and mixture was filtered on celite. The aq. layer was extracted with CH2Cl2 (2X500mL). The organic layer was dried on MgSO4, filtered and concentrated to dryness to afford the crude product. This product was purified by flash chromatography on silica gel eluting with ethyl acetate - methanol (92-8), the solvents were evaporated to dryness to afford 1-(4-(4-meth
The source
This record comes from experimental reaction archive (ord-8b6e9d49ac804667b43344fcaf4ab862). Open the source and check it against what is on this page.
experimental reaction archive record ord-8b6e9d49ac804667b43344fcaf4ab862 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
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