Buchwald–Hartwig amination, record ord-fb5c3a40f09e4b5fab2cf5db4493aed4
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 | 4-Bromo-2-nitroanisole | C₇H₆BrNO₃ | |
| Reactant | rel-(2R,6S)-2,6-dimethylpiperazine | C₆H₁₄N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | cis-3,5-Dimethyl-1-[4-(methyloxy)-3-nitrophenyl]piperazine | C₁₃H₁₉N₃O₃ | 55.97% |
Conditions
- Temperature
- 100 °C
Yield
- 56% of cis-3,5-Dimethyl-1-[4-(methyloxy)-3-nitrophenyl]piperazine.
Procedure
Copied from the source record, unedited
To a solution of 4-bromo-1-methoxy-2-nitrobenzene (150 mg, 0.65 mmol) in dioxane (4 mL) was added (2R,6S)-2,6-dimethylpiperazine (221 mg, 1.94 mmol) followed by cesium carbonate (316 mg, 0.97 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (56.4 mg, 0.09 mmol) and diacetoxypalladium (14.51 mg, 0.06 mmol). The resulting mixture was heated at 100 °C under argon over night (black). LCMS Ok. The solids were filtered through celite and washed with ethyl acetate. The ethyl acetate was evaporated under reduced pressure and the crude product was purified by flash- chromatograpy eluated with dichloromethane/ Methanol + 0.2% Et3N 100/0 =>90/10 over 20 min. The pure fractions was collected and concentrated to give (3R,5S)-1-(4-methoxy-3-nitrophenyl)-3,5-dimethylpiperazine (96 mg, 56.0 %) as red so
The source
This record comes from experimental reaction archive (ord-fb5c3a40f09e4b5fab2cf5db4493aed4). Open the source and check it against what is on this page.
experimental reaction archive record ord-fb5c3a40f09e4b5fab2cf5db4493aed4 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.