Potassium Carbonate → HCID 43610331, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tetrahydropyran-4-ylamine (0.75 g, 7.44 mmol) in DMF (2 mL) was added to a mixture of 1-fluoro-2-nitrobenzene (1.00 g, 7.09 mmol) and potassium carbonate (2.94 g, 21.3 mmol) in DMF (10 mL). The reaction mixture was heated for 1 h at 135° C. under microwave irradiation and then volatiles were removed in vacuo. The resulting residue was partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc (×2) and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo affording (2-Nitrophenyl)(tetrahydropyran-4-yl)amine as a yellow solid (1.58 g, quantitative). 1H NMR (CDCl3, 400 MHz): δ 8.18 (1H, d, J=8.65 Hz), 8.09 (1H, s), 7.42 (1H, t, J=7.81 Hz), 6.87 (1H, d, J=8.70 Hz), 6.64 (1H, t, J=7.72), 4.06-3.98 (2H, m), 3.79-3.68 (1H, m), 3.57 (2H, t, J=11.32 Hz), 2.14-2.01 (2H, m), 1.74-1.61 (2H, m).

Provenance & Evidence