Buchwald–Hartwig amination, record ord-3ee1bec4d5b244e8a0d82f023c1c6526
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 | 2-Bromo-N,N-dimethylaniline | C₈H₁₀BrN | |
| Reactant | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl | C₃₀H₄₃O₂P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | Tert-butyl 4-[2-(dimethylamino)phenyl]piperazine-1-carboxylate | C₁₇H₂₇N₃O₂ | 31.99% |
Conditions
- Temperature
- 100 °C
Yield
- 32% of Tert-butyl 4-[2-(dimethylamino)phenyl]piperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
Palladium (II) acetate (67.3 mg, 0.30 mmol) and 2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (280 mg, 0.60 mmol) were dissolved in toluene (7 mL) and purged with nitrogen. The mixture was warmed to 50°C for 15 mins. In a separate vessel, were mixed 2-bromo-N,N-dimethylaniline (600 mg, 3.00 mmol), tert-butyl piperazine-1-carboxylate (559 mg, 3.00 mmol) and sodium-t- butoxide (432 mg, 4.50 mmol) in toluene (8 mL). The mixture was degassed and purged with nitrogen. The catalyst solution was added and the resulting mixture heated at 100°C overnight. The reaction mixture was filtered through celite, washing with MeOH/EtOAc. The filtrate was concentrated and purified by flash silica chromatography, elution gradient 0 to 70% EtOAc in heptane. Pure fractions were evaporated to drynes
The source
This record comes from experimental reaction archive (ord-3ee1bec4d5b244e8a0d82f023c1c6526). Open the source and check it against what is on this page.
experimental reaction archive record ord-3ee1bec4d5b244e8a0d82f023c1c6526 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.