Buchwald–Hartwig amination: 7-Bromo-1-benzofuran → 1-Benzofuran-7-yl-4-phenethyl-piperazine; hydrochloride
62% yield, run at 110 °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 | 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.
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.
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.
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