Buchwald–Hartwig amination: 3-Bromoanisole → 1-(3-Methoxyphenyl)piperidine-4-carbonitrile
28% yield, run at 100 °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 | 3-Bromoanisole | C₇H₇BrO | |
| Reactant | 4-Cyanopiperidine | C₆H₁₀N₂ | |
| Reagent | lithium bis(trimethylsilyl)azanide | C₆H₁₈LiNSi₂ | |
| Catalyst | 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane | C₁₈H₃₉N₄P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 1-(3-Methoxyphenyl)piperidine-4-carbonitrile | C₁₃H₁₆N₂O | 28.45% |
Conditions
- Temperature
- 100 °C
Yield
- 28% of 1-(3-Methoxyphenyl)piperidine-4-carbonitrile.
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
Reaction carried out by , work up and purification on this page. piperidine-4-carbonitrile (7.07 g, 64.16 mmol); 1-bromo-3-methoxybenzene (6.77 mL, 53.47 mmol) and diacetoxypalladium (2.401 g, 10.69 mmol) were thoroughly placed under an inert atmoshere. To this was added 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.732 g, 2.14 mmol); LITHIUM BIS(TRIMETHYLSILYL)AMIDE (123 mL, 122.97 mmol) and toluene (20 mL). The resultant mixture was stirred overnight at 100 °C (suspect that it did not need overnight. The reaction mixture was poured onto DCM (200 mL), the mixture was filtered through celite and evaporated to afford a black residue. This was suspended in EtOAc (200 mL) and water (20 mL) and filtered through a pad of silica, washing through with EtOAc (300 mL) and w
The source
This record comes from experimental reaction archive (ord-11b483655b194597ac2e93597b6914d4). Open the source and check it against what is on this page.
experimental reaction archive record ord-11b483655b194597ac2e93597b6914d4 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
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