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

HRID 419407Notes

Reaction equation

[CH:1]([S:3]([CH3:6])(=[O:5])=[O:4])=[CH2:2].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:18]2[CH2:23][CH2:22][CH:21]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH2:20][CH:19]=2)[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16]>O1CCOCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:18]2[CH2:23][CH2:22][CH:21]([N:24]3[CH2:29][CH2:28][N:27]([CH2:2][CH2:1][S:3]([CH3:6])(=[O:5])=[O:4])[CH2:26][CH2:25]3)[CH2:20][CH:19]=2)[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16]

Participants

Conditions

Temperature: 95 °C

Procedure

A solution of methyl vinyl sulfone (201 mg, 1.89 mmol) and 1-{4-[3-(methyloxy)-4-nitrophenyl]-3-cyclohexen-1-yl}piperazine (200 mg, 0.63 mmol) was stirred in dioxane (6 mL) under N2. The reaction was then heated to 95° C. and stirred for approximately 3 h. The reaction was then cooled to rt and concentrated under vacuum. The residue was taken up in DCM and aqueous (saturated) NaHCO3. The aqueous layer was extracted with DCM (2×). The combined organic layers were dried over MgSO4, filtered, then concentrated and purified by silica gel chromatography to give the title compound of step G (222 mg, 0.52 mmol, 83%) as a light yellow solid. MS (ESI): 424 [M+H]+.

Workup

temperatureThe reaction was then cooled to rt
concentrationconcentrated under vacuum
extractionThe aqueous layer was extracted with DCM (2×)
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-6c7389cb3b414f4ba201dcdabbfa96e4
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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