Buchwald–Hartwig amination: 1-Bromo-4-iodobenzene → 1-(4-Bromophenyl)-cis-3,5-dimethylpiperazine

Drawn from the record's atom map: which bonds break and which form between the reactants and products the source listed. It shows a change in connectivity, not a simulated trajectory and not a mechanism.

Temperature

90 °C

Only the dimensions the source stated are listed. Anything absent here was not recorded, and it is not inferred from what the class usually needs.

Copied from the source record, unedited

sodium 2-methylpropan-2-olate (0.510 g, 5.30 mmol) was added to (2R,6S)-2,6-dimethylpiperazine (0.605 g, 5.30 mmol) in dioxane (40 mL) at 21°C under nitrogen. Stirred for 5 mins. 1-bromo-4-iodobenzene (1 g, 3.53 mmol) added, followed by diacetoxypalladium (0.079 g, 0.35 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.409 g, 0.71 mmol). Reaction evacuated and refilled with nitrogen several times. Heated at 90C for 18hours. left to cool o/w. The reaction mixture was diluted with EtOAc (250 mL), and washed sequentially with water (150 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 30% MeOH in EtOAc. Pure fractions were evaporated to dryn

This record comes from experimental reaction archive (ord-609b92e7f381461a936ff9653aaca797). Open the source and check it against what is on this page.

• experimental reaction archive record ord-609b92e7f381461a936ff9653aaca797 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.

  experimental record · quality medium · source

experimental reaction record.