Buchwald–Hartwig amination: Bromobenzene → tert-butyl N-[2-(1-phenylpiperidin-4-yl)ethyl]carbamate
0% yield, run at 50 °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 | Bromobenzene | C₆H₅Br | |
| Reactant | 4-(2-Aminoethyl)piperidine, 4-BOC protected | C₁₂H₂₄N₂O₂ | |
| 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 | tert-butyl N-[2-(1-phenylpiperidin-4-yl)ethyl]carbamate | C₁₈H₂₈N₂O₂ | 0% |
Conditions
- Temperature
- 50 °C
Yield
- 0% of tert-butyl N-[2-(1-phenylpiperidin-4-yl)ethyl]carbamate.
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 |
|---|---|---|---|---|---|---|
| Iodobenzene; 4-(2-Aminoethyl)piperidine, 4-BOC protected | Tris(1,1-dimethylethyl)phosphine; Bis(tri-tert-butylphosphine)palladium(0) | Potassium Phosphate, Tribasic | 1,2-Dimethoxyethane | 100 °C | — | 0% |
| Bromobenzene; 4-(2-Aminoethyl)piperidine, 4-BOC protected | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | sodium 2-methylpropan-2-olate | Toluene | 50 °C | — | 0% (this run) |
Procedure
Copied from the source record, unedited
palladium(II) acetate (21.45 mg, 0.10 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (111 mg, 0.19 mmol) were placed in a round-bottomed vessel that was filled with nitrogen. Toluene (0.8 mL) was added and the mixture was heated to 50°C for 30 min. sodium tert-butoxide (138 mg, 1.43 mmol) was added to a second vessel and inerted with nitrogen. tert-butyl 2-(piperidin-4-yl)ethylcarbamate (342 mg, 1.5 mmol) and bromobenzene (150mg, 0.96 mmol) and toluene (1.4 mL) were added. 14/04 2009 13:57:24 +0200 The catalyst solution was added to the reagent mixture and the combined mixture was heated to reflux for several hours. The reaction did not work.
The source
This record comes from experimental reaction archive (ord-59ade4a657944ddaa87cf04392b14d28). Open the source and check it against what is on this page.
experimental reaction archive record ord-59ade4a657944ddaa87cf04392b14d28 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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