Cyclohexanemethylamine → 4-[(Cyclohexylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

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Reaction Steps

4-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide (107 mg, 0.307 mmol) and cyclohexylmethylamine (0.050 mL, 0.368 mmol) were stirred in 3 mL of EtOH containing TEA (0.065 mL, 0.460 mmol) at 75° C. for 3 h. The mixture was concentrated. The residue was re-dissolved in EtOAc and washed with 5% KHSO4 solution, saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The title product was purified by flash chromatography using 9:1/hexanes:EtOAc. Yield: 113 mg (83%). 1H NMR (400 MHz, CDCl3) δ 1.05 (m, 2H), 1.24 (m, 4H), 1.69 (m, 2H), 1.75 (m, 2H), 1.83 (m, 1H), 3.17 (t, J=6.64 Hz, 2H), 4.23 (q, J=8.53 Hz, 4H), 6.91 (d, J=8.98 Hz, 1H), 7.51 (d, J=8.89 Hz, 1H), 8.28 (s, 1H), 8.39 (s, 1H).

Provenance & Evidence