Buchwald–Hartwig amination, record ord-5086568c313949c09e3b4fd70cc4de5e
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 | 2,4-Dichloro-1-iodobenzene | C₆H₃Cl₂I | |
| Reactant | 4-Piperidinemethanol | C₆H₁₃NO | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | [1-(2,4-Dichlorophenyl)piperidin-4-yl]methanol | C₁₂H₁₅Cl₂NO | 21.87% |
Conditions
- Temperature
- 125 °C
Yield
- 22% of [1-(2,4-Dichlorophenyl)piperidin-4-yl]methanol.
Procedure
Copied from the source record, unedited
**_Procedure:_** To a flask was added 1,3-Dichloro-4-iodobenzene (5.89 mL, 43.41 mmol), piperidin-4-ylmethanol (5 g, 43.41 mmol), cesium carbonate (28.3 g, 86.83 mmol), 18-Crown-6 (1.377 g, 5.21 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.811 g, 1.30 mmol), and toluene (50 mL). The mixture was stirred under nitrogen and Tris(dibenzylideneacetone)dipalladium(0) (0.398 g, 0.43 mmol) was added in one portion. The resultant yellow mixture was heated with oil bath temperature set at 125°C for 3 hours. LCMS shows desired product as well as other impurities. The reaction was cooled to room temperature. Ethyl acetate (2 x 200 mL) was added and the resultant mixture was extracted with saturated aqueous sodium chloride (200 mL). The organics were collected and dried over sodium sulfat
The source
This record comes from experimental reaction archive (ord-5086568c313949c09e3b4fd70cc4de5e). Open the source and check it against what is on this page.
experimental reaction archive record ord-5086568c313949c09e3b4fd70cc4de5e 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.