Dimethylformamide → Tert-butyl 4-(2-tert-butyl-4-cyanophenyl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 4-(4-bromo-2-tert-butylphenyl)piperazine-1-carboxylate (Example 85, 3.0 g, 7.55 mmol), zinc cyanide (1.77 g, 15.1 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.88 g, 0.76 mmol) in DMF (30 mL) was stirred at 100° C. for 4 h under argon atmosphere. The reaction mixture was cooled to room temperature, poured into saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to give the crude product. The product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=95:5 to 80:20) to provide tert-butyl 4-(2-tert-butyl-4-cyanophenyl)piperazine-1-carboxylate (2.29 g, 88%) as a white powder.

Provenance & Evidence