2-Ethylaniline → HCID 58949875, compound

Participants

Reaction Steps

To a solution of 100 mg (0.28 mmol) 8-benzyl-1-(3-fluorophenyl)-1,8-diazaspiro[4.5]decane-2,4-dione in 0.71 mL dry toluene was added 70 mg (0.37 mmol)p-toluenesulfonic acid monohydrate and 61 μL (0.50 mmol) 2-ethylaniline. The reaction was heated to reflux for 18 h and then diluted with EtOAc, washed with 1N NaOH, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified on silica gel with 20-60% EtOAc/hexanes to afford title example 8-benzyl-4-[(2-ethylphenyl)amino]-1-(3-fluorophenyl)-1,8-diazaspiro[4.5]dec-3-en-2-one as a tan foam. 1H NMR (CD3OD, 400 MHz) δ 7.43 (q, J=7.38 Hz, 1H), 7.32 (m, 1H), 7.24 (m, 6H), 7.16 (m, 3H), 7.08 (m, 2H), 4.55 (s, 1H), 3.41 (s, 2H), 2.80 (m, 2H), 2.64 (q, J=7.51 Hz, 2H), 2.38 (m, 2H), 2.19 (m, 2H), 2.10 (dt, J=11.5 and 3.85 Hz, 2H), 1.18 (t, J=7.51 Hz, 3H); LC/MS [M+H]=456.1.

Provenance & Evidence