Buchwald–Hartwig amination: Benzene, 1-bromo-3-methyl-2-nitro- → 4-(3-Methyl-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester

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

80 °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.

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.

• Methyl 4-(4-Boc-1-piperazinyl)-2-chlorobenzoate91%
• Tert-butyl 4-(7-benzo[b]furanyl)piperazine-1-carboxylate84%
• Tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate83%
• Tert-butyl 4-(4-cyanophenyl)piperazine-1-carboxylate82%
• Tert-butyl 4-(5-(benzyloxy)pyridin-2-YL)piperazine-1-carboxylate69%
• tert-Butyl 4-(2-(ethoxycarbonyl)benzofuran-4-yl)piperazine-1-carboxylate64%
• Tert-butyl 4-(2-methoxyphenyl)piperazine-1-carboxylate62%
• tert-butyl 4-(2-methyl-3-oxo-1H-isoindol-5-yl)piperazine-1-carboxylate57%
• Tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylate52%
• Tert-butyl 4-(3-chloro-4-cyanophenyl)piperazine-1-carboxylate47%
• tert-Butyl 4-(quinolin-2-yl)piperazine-1-carboxylate46%
• Tert-butyl 4-[6-[(4-methylsulfonylphenyl)methoxy]-3-pyridinyl]piperazine-1-carboxylate43%

Copied from the source record, unedited

tert-butyl piperazine-1-carboxylate (172 mg, 0.93 mmol) and 1-bromo-3-methyl-2-nitrobenzene (0.124 mL, 0.93 mmol), were added to a stirred solution of diacetoxypalladium (20.78 mg, 0.09 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (107 mg, 0.19 mmol) and cesium carbonate (664 mg, 2.04 mmol) dissolved in dioxane (3 mL). The resulting solution was stirred at 80 °C under nitrogen overnight. The reaction mixture was filtered, dried under vaccum. The crude product was purified by flash chromatography on silica gel eluting with 5 to 15% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford tert-butyl 4-(3-methyl-2-nitrophenyl)piperazine-1-carboxylate (50.0 mg, 16.81 %) as a orange oil.

This record comes from experimental reaction archive (ord-100bcab4f1bd45d89d76662307487cf4). Open the source and check it against what is on this page.

• experimental reaction archive record ord-100bcab4f1bd45d89d76662307487cf4 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.