Buchwald–Hartwig amination, record ord-2de77de369ef42f8b910f9e83130f454
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 | Methyl 3-bromobenzoate | C₈H₇BrO₂ | |
| Reactant | 4-(N-Boc-amino)piperidine | C₁₀H₂₀N₂O₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | Methyl 3-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}benzoate | C₁₈H₂₆N₂O₄ | 13.76% |
Conditions
- Temperature
- 100 °C
Yield
- 14% of Methyl 3-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}benzoate.
Procedure
Copied from the source record, unedited
All chemicals were mixed in a 50 mL round bottom flask. The solids were degassed and placed under nitrogen. Toluene was added and the mixture was stirred at 100°C for 24 h. Cooled and filtered. The filtrate was concentrated under vacuum. Crude product was mainly starting material but some product had been formed. The product was purified by silica gel chromatography using 1-4% methanol/DCM. Product was slightly more polar than starting material bromide. There was obtained 230 mg of the desired product as a solid. HNMR and LC MS ok.
The source
This record comes from experimental reaction archive (ord-2de77de369ef42f8b910f9e83130f454). Open the source and check it against what is on this page.
experimental reaction archive record ord-2de77de369ef42f8b910f9e83130f454 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.