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

HRID 419489Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2].[CH:19]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH2:20]>O1CCOCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:14][CH2:15][N:16]([CH2:20][CH2:19][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][CH2:18]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

To 1-[3-(ethyloxy)-4-nitrophenyl]piperazine (0.5 g, 1.99 mmol) in 10 mL of dioxane was added, methyl vinyl sulfone (0.53 g, 4.97 mmol). The mixture was heated to 120° C. for 2 h. The solvent was rotovaped down and the crude product was purified by flash chromatography to give the title compound of step B (0.565 g, 1.58 mmol, 79%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.83 (d, J=9.34 Hz, 1H), 6.57 (dd, J=9.43, 2.47 Hz, 1H), 6.51 (d, J=2.38 Hz, 1H), 4.16 (q, J=6.96 Hz, 2H), 3.36-3.41 (m, 4H), 3.30-3.34 (m, 2H), 3.01 (s, 3H), 2.73 (t, J=6.87 Hz, 2H), 2.49-2.55 (m, 4H), 1.32 (t, J=6.96 Hz, 3H).

Workup

customthe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-2d8dc24faced415b8dd82b331308a44e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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