Buchwald–Hartwig amination: 4-Bromo-2-nitroanisole → 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanone
83% yield, run at 120 °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 | 82.89% |
Conditions
- Temperature
- 120 °C
Yield
- 83% of 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanone.
Procedure
Copied from the source record, unedited
1-(piperazin-1-yl)ethanone (9.94 g, 77.58 mmol), Cesium carbonate (50.6 g, 155.15 mmol), XANTPHOS (5.39 g, 9.31 mmol) and Pd(OAc)2 (1.393 g, 6.21 mmol) were added to a stirred solution of 4-bromo-1-methoxy-2-nitrobenzene (18 g, 77.58 mmol) dissolved in dioxane (120 ml). The resulting suspension was heated to 120 °C (bath) over a period of 1 hour. The reaction mixture was allowed to cool and the residual cesium carbonate was removed by filtration through a pad of Dicalite speed plus, washing with dichloromethane. The solvent was removed under reduced pressure to give a dark oil. PBO-02628-53-01 w= 45 g The crude product in solution in DCM was added to a silica gel column and was eluted with methanol 0 to 20% in EtOAc (NOVASEP). Collected fractions to dryness to afford 1-(4-(4-methoxy-3-ni
The source
This record comes from experimental reaction archive (ord-7efc5b9774d04fb09dba803fb4f7b480). Open the source and check it against what is on this page.
experimental reaction archive record ord-7efc5b9774d04fb09dba803fb4f7b480 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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