Buchwald–Hartwig amination: 1-Bromo-4-fluorobenzene → 1-Benzyl-4-(4-fluorophenyl)piperazine
75% yield, run at 50 °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 | 1-Bromo-4-fluorobenzene | C₆H₄BrF | |
| Reactant | 1-Benzylpiperazine | C₁₁H₁₆N₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 1-Benzyl-4-(4-fluorophenyl)piperazine | C₁₇H₁₉FN₂ | 74.98% |
Conditions
- Temperature
- 50 °C
Yield
- 75% of 1-Benzyl-4-(4-fluorophenyl)piperazine.
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.
- 7-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide52%
- 8-(4-Benzyl-piperazin-1-yl)-6-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester48%
- Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate27%
- 4-(4-Fluorophenyl)piperazin-2-one0%
- Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate0%
- Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate0%
Procedure
Copied from the source record, unedited
diacetoxypalladium (12.74 mg, 0.06 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (32.8 mg, 0.06 mmol) were suspended in toluene (0.5 mL) under N2. Heated to 50C for 30 min (microwave). sodium 2-methylpropan-2-olate (109 mg, 1.13 mmol) was suspended in toluene (0.500 mL) under N2. 1-benzylpiperazine (0.099 mL, 0.57 mmol) and 1-bromo-4-fluorobenzene (0.093 mL, 0.85 mmol) were added, followed by the catalyst solution. Heated to 100C for 2h in the microwave (high abs), then rt over night. The product was purified on silica (0-25% EtOAc/heptane) Yield: 1-benzyl-4-(4-fluorophenyl)piperazine (115 mg, 75.0 %)
The source
This record comes from experimental reaction archive (ord-8809d217cb404d41bb5809dd5f95b269). Open the source and check it against what is on this page.
experimental reaction archive record ord-8809d217cb404d41bb5809dd5f95b269 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.
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