Buchwald–Hartwig amination, record ord-587e8b015ef542aa9ba95a064a0d6902
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 | Benzonitrile, 4-bromo- | C₇H₄BrN | |
| Reactant | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Tetrahydrofuran | C₄H₈O | |
| Product | Tert-butyl 4-(4-cyanophenyl)piperazine-1-carboxylate | C₁₆H₂₁N₃O₂ | 82.34% |
Conditions
- Temperature
- 120 °C
Yield
- 82% of Tert-butyl 4-(4-cyanophenyl)piperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
To 4-bromobenzonitrile (.5 g, 2.75 mmol) dissolved in dry THF (10 mL) was added tert-butyl piperazine-1-carboxylate (0.512 g, 2.75 mmol), Sodium-t- butoxide (0.792 g, 8.24 mmol) and purged with N2 gas for 10 min followed by the addition of 2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl (0.131 g, 0.27 mmol)and Palladium II acetate (0.062 g, 0.27 mmol). The contents were further purged with N2 gas for further 10 min and heated at 85 °C for 2 h. The reaction mass was concentrated and the reside diluted with water and extracted with ethyl acetate . The combined organic extracts were washed with brine solution and dried over anhydrous sodium sulphate. The organic layer was evaporated under reduced pressure to obtain the crude product which was purified by 60-120 mesh silica gel c
The source
This record comes from experimental reaction archive (ord-587e8b015ef542aa9ba95a064a0d6902). Open the source and check it against what is on this page.
experimental reaction archive record ord-587e8b015ef542aa9ba95a064a0d6902 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.