Methyl vinyl sulfone → 1-[3-(Methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperazine

HRID 419468Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[CH:18]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH2:19]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH2:19][CH2:18][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 120 °C

Procedure

To 1-[3-(methyloxy)-4-nitrophenyl]piperazine (0.4 g, 1.74 mmol) in 10 mL of dioxane was added, methyl vinyl sulfone (0.46 g, 4.34 mmol). The mixture was heated to 120° C. for 1 h. The solvent was rotovaped down and the crude product was purified by flash chromatography to give the title compound of step B (0.55 g, 1.6 mmol, 92%). 1H NMR (400 MHz, CDCl3) δ ppm 7.97 (d, J=9.34 Hz, 1H), 6.41 (dd, J=9.34, 2.56 Hz, 1H), 6.31 (d, J=2.38 Hz, 1H), 3.93 (s, 3H), 3.36-3.43 (m, 4H), 3.19 (t, J=6.41 Hz, 2H), 3.03 (s, 3H), 2.92-2.99 (m, 2H), 2.60-2.68 (m, 4H).

Workup

customthe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-2d9bfb6f03bd439b9edf2c45ff91c5c5
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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