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

Participants

Reaction Conditions

Reaction Steps

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 provide pure tert-butyl 1-(3-nitrophenyl)piperidin-4-ylcarbamate (0.901 g, 56.6 %) as a light yellow solid.

Provenance & Evidence