Buchwald–Hartwig amination: Iodobenzene → tert-butyl N-[2-(1-phenylpiperidin-4-yl)ethyl]carbamate
0% 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 | Iodobenzene | C₆H₅I | |
| Reactant | 4-(2-Aminoethyl)piperidine, 4-BOC protected | C₁₂H₂₄N₂O₂ | |
| Reagent | Potassium Phosphate, Tribasic | K₃O₄P | |
| Catalyst | Tris(1,1-dimethylethyl)phosphine | C₁₂H₂₇P | |
| Catalyst | Bis(tri-tert-butylphosphine)palladium(0) | C₂₄H₅₄P₂Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | tert-butyl N-[2-(1-phenylpiperidin-4-yl)ethyl]carbamate | C₁₈H₂₈N₂O₂ | 0% |
Conditions
- Temperature
- 100 °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% (this run) |
| 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% |
Procedure
Copied from the source record, unedited
To a solution of tert-butyl 2-(piperidin-4-yl)ethylcarbamate (0.342 g, 1.5 mmol) in anhydrous DME were added iodobenzene (0.444 g, 2.18 mmol), bis(tri-t- butylphosphine)palladium(0) (0.077 g, 0.15 mmol) and potassium phosphate (0.245 mL, 3.00 mmol). The reaction was heated to 100°C overnight. This reaction did not work.
The source
This record comes from experimental reaction archive (ord-cc832050b1854993a53bbd02bde64312). Open the source and check it against what is on this page.
experimental reaction archive record ord-cc832050b1854993a53bbd02bde64312 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.
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