Methyl vinyl sulfone → 1-[2-(Methyloxy)-5-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperazine
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[CH:18]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH2:19]>CC(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:19][CH2:18][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:14][CH2:13]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The compound was synthesized by heating a solution of 1-[2-(methyloxy)-5-nitrophenyl]piperazine (0.5 g, 2.11 mmol) and methyl vinyl sulfone (0.336 g, 3.16 mmol) in iPrOH (25 mL) to reflux overnight. Reaction was cooled to rt and dried directly onto silica gel. Purified by silica gel chromatography 0-20% MeOH/NH4OH in EtOAc to obtain 0.5 g (69% yield) of the desired compound as a solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 2.6 (m, 4H) 2.7 (t, J=6.8 Hz, 2H) 3.0 (m, 8H) 3.9 (s, 3H) 7.1 (d, J=9.0 Hz, 1H) 7.6 (d, J=2.7 Hz, 1H) 7.9 (dd, J=9.1, 2.8 Hz, 1H).