Methyl vinyl sulfone → 2-(Methyloxy)-4-{1-[2-(methylsulfonyl)ethyl]-4-piperidinyl}aniline
Reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:4]=1[NH2:5].[CH:16]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH2:17]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:17][CH2:16][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:4]=1[NH2:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 2-(methyloxy)-4-(4-piperidinyl)aniline (0.50 g, 2.4 mmol) in DCM (5 mL) was added methyl vinyl sulfone (0.25 g, 2.4 mmol). The mixture was stirred in a sealed tube overnight. Silica gel was added, the solvent was removed under vacuum, and the material was purified by silica gel chromatography. The desired fractions were combined and rotovaped to give the title compound of step B (0.45 g, 1.4 mmol, 58%) as an oil. 1H NMR (400 MHz, CDCl3) 6 1H NMR (400 MHz, d6-DMSO) δ 6.63-6.57 (m, 3H), 3.79 (s, 3H), 3.71 (br s, 2H), 3.13 (t, J=6.6 Hz, 2H), 3.01 (s, 3H), 2.97 (d, J=11.4 Hz, 2H), 2.83 (t, J=6.6 Hz, 2H), 2.42-2.32 (m, 1H), 2.15-2.04 (m, 2H), 1.80 (d, J=12.1 Hz, 2H), 1.69-1.57 (m, 2H).