Buchwald–Hartwig amination, record ord-57be3c43ca2f40d482cab5a1bd42b5d5
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 2-Bromo-6-nitrotoluene | C₇H₆BrNO₂ | |
| 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 | Toluene | C₇H₈ | |
| Product | 1-[4-(2-Methyl-3-nitrophenyl)piperazin-1-yl]ethanone | C₁₃H₁₇N₃O₃ | 98.46% |
Conditions
- Temperature
- 100 °C
Yield
- 98% of 1-[4-(2-Methyl-3-nitrophenyl)piperazin-1-yl]ethanone.
Procedure
Copied from the source record, unedited
1-bromo-2-methyl-3-nitrobenzene (500 mg, 2.31 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (201 mg, 0.35 mmol) and cesium carbonate (1131 mg, 3.47 mmol) and diacetoxypalladium (52.0 mg, 0.23 mmol) were dissolved in toluene (10 mL) and sealed into a microwave tube degazed and purged with argon. The reaction was heated to 100 °C, over a period of 12 hours. The reaction mixture was cooled down to room temperature, filtered and the residue was evaporated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 10% methanol in dichloromethane. The solvent was evaporated to dryness to afford 1-(4-(2-methyl-3-nitrophenyl)piperazin-1-yl)ethanone (600 mg, 98 %) as a solid.
The source
This record comes from experimental reaction archive (ord-57be3c43ca2f40d482cab5a1bd42b5d5). Open the source and check it against what is on this page.
experimental reaction archive record ord-57be3c43ca2f40d482cab5a1bd42b5d5 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.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.