Buchwald–Hartwig amination, record ord-7b12b51966524113889660895d5b1caa
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 | 1-Bromo-2-chlorobenzene | C₆H₄BrCl | |
| Reactant | Piperazine | C₄H₁₀N₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 1-(2-Chlorophenyl)piperazine | C₁₀H₁₃ClN₂ | 43.8% |
Conditions
- Temperature
- 110 °C
Yield
- 44% of 1-(2-Chlorophenyl)piperazine.
Procedure
Copied from the source record, unedited
To a stirred sol of 1-bromo-2-chlorobenzene (0.606 mL, 5.22 mmol) in toluene (10 mL) was added Pd2(dba)3 (0.239 g, 0.26 mmol), BINAP (0.163 g, 0.26 mmol), sodium tert-butoxide (0.753 g, 7.83 mmol) and piperazine (1.350 g, 15.67 mmol) and the resulting sol was heated at 110 °C for 16h. Cooled to rt, filtered through a celeite pad, volatiles were evaporated off and residue was column chromatographed (DCM:MeOH 90:10) to afford 1-(2-chlorophenyl)piperazine (0.450 g, 43.8 %) as a gum.
The source
This record comes from experimental reaction archive (ord-7b12b51966524113889660895d5b1caa). Open the source and check it against what is on this page.
experimental reaction archive record ord-7b12b51966524113889660895d5b1caa 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.