Potassium Carbonate → (2-Nitrophenyl)(tetrahydropyran-3-yl)amine

Participants

Reaction Conditions

Reaction Steps

A solution of tetrahydropyran-3-ylamine (0.43 g, 4.05 mmol) in DMF (2 mL) was added to a mixture of 1-fluoro-2-nitrobenzene (0.57 g, 4.05 mmol) and potassium carbonate (1.68 g, 12.1 mmol) in DMF (10 mL). The reaction mixture was heated for 1 h at 135° C. under microwave irradiation. Additional tetrahydropyran-3-ylamine (40 mg) was added and microwave irradiation at 135° C. was continued for further 30 min. Volatiles were then removed in vacuo and 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. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-2% MeOH in DCM) affording (2-Nitrophenyl)(tetrahydropyran-3-yl)amine as an orange oil (0.73 g, 81%). LCMS: RT 3.31 min [M+H]+ 223.2.

Provenance & Evidence