Buchwald–Hartwig amination: 2-Chloroanisole → Tert-butyl 4-(2-methoxyphenyl)piperazine-1-carboxylate
11% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below. One of 2 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 2-Chloroanisole | C₇H₇ClO | |
| Reactant | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl | C₃₀H₄₃O₂P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | Tert-butyl 4-(2-methoxyphenyl)piperazine-1-carboxylate | C₁₆H₂₄N₂O₃ | 11.22% |
Conditions
- Temperature
- 100 °C
Yield
- 11% of Tert-butyl 4-(2-methoxyphenyl)piperazine-1-carboxylate.
Every recorded run making this product
2 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Reactants | Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|---|
| 2-Bromoanisole; tert-Butyl piperazine-1-carboxylate | Binap, (A+-)-; Bis(dibenzylideneacetone)palladium | sodium 2-methylpropan-2-olate | Toluene | 100 °C | — | 62% |
| 2-Chloroanisole; tert-Butyl piperazine-1-carboxylate | 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl; Palladium (II) acetate | sodium 2-methylpropan-2-olate | Toluene | 100 °C | — | 11% (this run) |
Procedure
Copied from the source record, unedited
RuPhos (32.7 mg, 0.07 mmol) and palladium (II) acetate (15.75 mg, 0.07 mmol) were suspended in toluene (1 mL) at ambient temperature. The mixture was degassed and purged with nitrogen several times and warmed to 50°C for 20 mins. In a separate vessel were mixed 1-chloro-2-methoxybenzene (100 mg, 0.70 mmol), tert-butyl piperazine-1-carboxylate (131 mg, 0.70 mmol), sodium tertbutoxide (101 mg, 1.05 mmol) and toluene (2 mL). The suspension was degassed and purged with nitrogen then warmed to 50°C. The solution of catalyst was added to the reaction vessel and the resulting mixture was degassed and purged with nitrogen. The reaction was heated to 110°C (ext T) under nitrogen for 6 hours then allowed to cool to ambient temperature overnight. The reaction mixture was filtered and concentrated
The source
This record comes from experimental reaction archive (ord-7d6438f5772442a8addd4f9357140a8b). Open the source and check it against what is on this page.
experimental reaction archive record ord-7d6438f5772442a8addd4f9357140a8b 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.