Buchwald–Hartwig amination: Benzene, 1-bromo-3-nitro- → tert-butyl N-[1-(3-nitrophenyl)piperidin-4-yl]carbamate

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

95 °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 3-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}benzoate14%

Copied from the source record, unedited

A 100 mL round bottom flask was charged with a magnetic stir bar, 1-bromo-3-nitrobenzene (1.000 g, 4.95 mmol), [Reactants], Pd2dba3 (0.227 g, 0.25 mmol), BINAP (0.308 g, 0.50 mmol), Cs2CO3 (4.03 g, 12.38 mmol), and toluene (19.80 ml). The vessel was capped with a septum, placed under an atmosphere of argon, and placed in an oil bath heated to 95 °C. The reaction was allowed to stir at this temperature for 16 h before being allowed to cool to rt. The reaction mixture was poured into a separatory funnel containing water (~100 mL) and extracted with ethyl acetate ( 2 x 100 mL). The combined organic extract was dried with MgSO4, filtered, and conc. _in vacuo_ to yield the crude product which was purified via silica gel chromatography (80 g) using ethyl acetate/hexanes (1:5) as eluent to provid

This record comes from experimental reaction archive (ord-14a2a1784ff04475ad4db1893eca50ce). Open the source and check it against what is on this page.

• experimental reaction archive record ord-14a2a1784ff04475ad4db1893eca50ce 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.