Buchwald–Hartwig amination, record ord-bd4700a79525457dbcfd3c5e1368118f
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 | Bromobenzene | C₆H₅Br | |
| Reactant | 2-Phenylpiperidine | C₁₁H₁₅N | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl | C₃₀H₄₃O₂P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 1,2-Diphenylpiperidine | C₁₇H₁₉N | 15.56% |
Conditions
- Temperature
- 100 °C
Yield
- 16% of 1,2-Diphenylpiperidine.
Procedure
Copied from the source record, unedited
Caesium carbonate (556 mg, 1.71 mmol) was added to bromobenzene (0.060 mL, 0.57 mmol) and 2-phenylpiperidine (110 mg, 0.68 mmol) in 1,4-dioxane (2 mL). The reaction was degassed and Tris(dibenzylideneacetone)?dipalladium(0) (13.01 mg, 0.01 mmol) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (RuPhos) (13.26 mg, 0.03 mmol) were added. The resulting solution was stirred at 100 °C for 16 hours. LCMS showed The reaction mixture was diluted with EtOAc, and washed with water. The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 15% MeOH in DCM. Pure fractions were evaporated to dryness to afford 1,2-diphenylpiperidine (21.00 mg, 15.56 %) as a yellow oil.
The source
This record comes from experimental reaction archive (ord-bd4700a79525457dbcfd3c5e1368118f). Open the source and check it against what is on this page.
experimental reaction archive record ord-bd4700a79525457dbcfd3c5e1368118f 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.