Buchwald–Hartwig amination, record ord-a9eb8bf838c248b3ad5908714b48274f
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 | 5-Chloro-2-iodoanisole | C₇H₆ClIO | |
| Reactant | 1-Methylpiperazine | C₅H₁₂N₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 1-(4-Chloro-2-methoxyphenyl)-4-methylpiperazine | C₁₂H₁₇ClN₂O | 0% |
Conditions
- Temperature
- 80 °C
Yield
- 0% of 1-(4-Chloro-2-methoxyphenyl)-4-methylpiperazine.
Procedure
Copied from the source record, unedited
1-methylpiperazine (0.021 mL, 0.19 mmol) was added to 4-chloro-1-iodo-2-methoxybenzene (50 mg, 0.19 mmol) and sodium 2-methylpropan-2-olate (35.8 mg, 0.37 mmol) in toluene (0.650 mL) and the solution degassed. rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (11.60 mg, 0.02 mmol) and Palladium II acetate (4.18 mg, 0.02 mmol) were added to the resulting mixture and the vial stirred at 80 °C for 17 hours. LCMS revelead product peak, but not great. Product not isolated.
The source
This record comes from experimental reaction archive (ord-a9eb8bf838c248b3ad5908714b48274f). Open the source and check it against what is on this page.
experimental reaction archive record ord-a9eb8bf838c248b3ad5908714b48274f 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.