Buchwald–Hartwig amination, record ord-856e3e504ed54d0cb8cb9c559a0474c7
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 | Ethyl 4-bromobenzoate | C₉H₉BrO₂ | |
| Reactant | Piperidine | C₅H₁₁N | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Ethyl 4-(piperidin-1-yl)benzoate | C₁₄H₁₉NO₂ | 81.44% |
Conditions
- Temperature
- 80 °C
Yield
- 81% of Ethyl 4-(piperidin-1-yl)benzoate.
Procedure
Copied from the source record, unedited
In a 250 mL round-bottomed flask was ethyl 4-bromobenzoate (816 µl, 5 mmol), piperidine (593 µl, 6.00 mmol), and CESIUM CARBONATE (2444 mg, 7.50 mmol) in dioxane (2.36E+04 µl) to give a white suspension. The solution was degassed with N2 (g) for 15 min and then added BINAP (156 mg, 0.25 mmol) and PALLADIUM(II) ACETATE (56.1 mg, 0.25 mmol). The reaction was heated to 100 °C and stirred under a reflux condenser overnight. The reaction was checked by LC-MS (complete), filtered, rinsed with DCM, concentrated in vacuo and onto silica gel. Purification by Iscos (25 g.) using 100% hexanes -> 40% EtOAc in Hexanes afforded a white solid. 950 mg of a white solid obtained. 1H NMR (300 MHz, DMSO- _d_ 6) d ppm 1.28 (t, _J_ =7.08 Hz, 3 H) 1.58 (s, 6 H) 3.31 - 3.38 (m, 4 H) 4.23 (q, _J_ =7.11 Hz, 2 H) 6
The source
This record comes from experimental reaction archive (ord-856e3e504ed54d0cb8cb9c559a0474c7). Open the source and check it against what is on this page.
experimental reaction archive record ord-856e3e504ed54d0cb8cb9c559a0474c7 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.