Buchwald–Hartwig amination: 2-Bromo-4-chlorobenzonitrile → 4-Chloro-2-(piperazin-1-yl)benzonitrile
0% yield, run at 90 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 2-Bromo-4-chlorobenzonitrile | C₇H₃BrClN | |
| Reactant | Piperazine | C₄H₁₀N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 4-Chloro-2-(piperazin-1-yl)benzonitrile | C₁₁H₁₂ClN₃ | 0% |
Conditions
- Temperature
- 90 °C
Yield
- 0% of 4-Chloro-2-(piperazin-1-yl)benzonitrile.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
- 4-chloro-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]benzonitrile69%
- tert-butyl N-[2-chloro-5-(piperazin-1-yl)phenyl]carbamate57%
- 1-(2,2-Difluoro-2H-1,3-benzodioxol-5-YL)piperazine51%
- 4-(2-Fluoro-4-methylphenylamino)-7-(piperazin-1-yl)cinnoline-3-carbonitrile51%
- 1-(2-Chlorophenyl)piperazine44%
- 1-(4-Methyl-3-nitrophenyl)piperazine39%
- 1-(Pyridin-3-yl)piperazine0%
- 4-Piperazin-1-yl-1-benzofuran-2-carboxamide0%
- 4-Fluoro-2-(piperazin-1-yl)benzonitrile0%
Procedure
Copied from the source record, unedited
Tris(dibenzylideneacetone)dipalladium (0) (43.4 mg, 0.05 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (59.0 mg, 0.09 mmol) were added to a mixture of 2-bromo-4-chlorobenzonitrile (205 mg, 0.95 mmol), Cesium carbonate (463 mg, 1.42 mmol) and Piperazine (163 mg, 1.89 mmol) in dioxane (3 mL). Reaction vessel was placed in an oil bath set to 90 °C 2.45pm. LCMS o/n shows large product peak (222). Cooled, filtered through a silica plug, washing with EtOAc until filtrate is clear. Crude NMR is very messy, target deprioritized. Discarded.
The source
This record comes from experimental reaction archive (ord-124e8e40d3e54042af531dbb1d8d85d1). Open the source and check it against what is on this page.
experimental reaction archive record ord-124e8e40d3e54042af531dbb1d8d85d1 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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
Open in the Reaction Lab
The atom map, the bonds that break and form, and records running the same transformation.
Percent yield calculator
Work out a yield from what you isolated against what the equation allows.
Molecules A–Z
Every named molecule, with its identifiers and sources.