Potassium Carbonate → 1-Boc-4-(2-formylphenyl)piperazine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-fluorobenzaldehyde (Aldrich) (1 g, 8.1 mmol) in DMF (14 mL) was added 1-Boc-piperazine (Lancaster) (2.3 g, 12 mmol). The resulting solution was treated with copper (Aldrich Chemical Company) (50 mg, 0.8 mmol) and K2CO3 (Aldrich) (5.1 g, 37 mmol). The suspension was heated in a sealed tube at 150° C. for 18 h. After cooling to RT, the reaction mixture was partitioned between EtOAc and brine. The aqueous layer was extracted twice with EtOAc and the combined EtOAc layers were washed with water, dried over Na2SO4, filtered and concentrated in vacuo. The crude compound was purified on a Biotage 40 M column (12% EtOAc in hexanes) to give tert-butyl 4-(2-formylphenyl)piperazinecarboxylate (0.66 g) as a yellow oil. MS m/z: 291 (M+H). Calc'd for C16H22N2O3: 290.36.

Provenance & Evidence