Buchwald–Hartwig amination, record ord-c7d1825ed35e4dffbc57a0b9b8fa9354
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 | p-Bromoacetophenone | C₈H₇BrO | |
| Reactant | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | Tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylate | C₁₇H₂₄N₂O₃ | 52.48% |
Conditions
- Temperature
- 120 °C
Yield
- 52% of Tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
In a CEM MW vial, p-Bromoacetophenone (729 ml, 6.03 mmol),tert-Butyl 1-piperazinecarboxylate (1.684 g, 9.04 mmol),racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.375 g, 0.60 mmol),Palladium (II) acetate (0.135 g, 0.60 mmol),Cesium carbonate (3.93 g, 12.06 mmol) was taken in toluene (10 ml).The RM was subjected to MW power of 300W,temp 120°C for 45 minutes. The LCMS was checked showed the formation of required mass. Work-up: The RM was passed through hyflow bed and filtrate was evaporated and chrmatographed using Ethyl acetate hexane to obtain tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylate (0.963 g, 52.5 %).
The source
This record comes from experimental reaction archive (ord-c7d1825ed35e4dffbc57a0b9b8fa9354). Open the source and check it against what is on this page.
experimental reaction archive record ord-c7d1825ed35e4dffbc57a0b9b8fa9354 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.