Buchwald–Hartwig amination, record ord-8cfc6888cfb048a3bbd7a788345f4499
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 | 7-Bromo-1-benzofuran | C₈H₅BrO | |
| Reactant | 1-Phenethylpiperazine | C₁₂H₁₈N₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 1-Benzofuran-7-yl-4-phenethyl-piperazine; hydrochloride | C₂₀H₂₂N₂O | 62.12% |
Conditions
- Temperature
- 110 °C
Yield
- 62% of 1-Benzofuran-7-yl-4-phenethyl-piperazine; hydrochloride.
Procedure
Copied from the source record, unedited
A dried Radley tube was charged with rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (6.32 mg, 10.15 µmol), Tris(dibenzylideneacetone)dipalladium(0) (4.65 mg, 5.08 µmol) and Sodium tert- butoxide (34.1 mg, 0.36 mmol). Argon atmosphere was introduced and toluene (3ml) was added followed by 7-bromobenzofuran (50mg, 0.25 mmol) and 1-phenethylpiperazine (48.3 mg, 0.25 mmol). The reaction mixture was heated at reflux over night. 2010-03-25 The reaction mixture was filtered, concentrated and purified by flash chromatography (Isolute Si 10g, heptane: ethyl acetate; 4:1) to give 1-(benzofuran-7-yl)-4-phenethylpiperazine (48.3 mg, 62.1 %)
The source
This record comes from experimental reaction archive (ord-8cfc6888cfb048a3bbd7a788345f4499). Open the source and check it against what is on this page.
experimental reaction archive record ord-8cfc6888cfb048a3bbd7a788345f4499 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.