Water → 1-[2-Ethyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl)piperazine

HRID 419568Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([O:12][CH3:13])=[CH:5][C:4]=1F)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:22][S:23]([CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)(=[O:25])=[O:24].O>CS(C)=O>[CH2:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([O:12][CH3:13])=[CH:5][C:4]=1[N:31]1[CH2:30][CH2:29][N:28]([CH2:27][CH2:26][S:23]([CH3:22])(=[O:24])=[O:25])[CH2:33][CH2:32]1)[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

1-Ethyl-2-fluoro-4-(methyloxy)-5-nitrobenzene (1.0 g, 5.0 mmol) was dissolved in DMSO (8 mL). Potassium carbonate (2.1 g, 15 mmol) and 1-[2-(methylsulfonyl)ethyl]piperazine hydrochloride (Example 148, step B) (1.1 g, 5.0 mmol) were added and the reaction mixture was heated to 65° C. and allowed to stir over the weekend. The mixture was then poured into water and extracted with EtOAc (2×). The combined organics were dried with MgSO4, filtered, and concentrated in vacuo to give the title compound without further purification (1.7 g, 4.7 mmol, 93%). MS (M+H, ES+) 372.

Workup

extractionextracted with EtOAc (2×)
dry with materialThe combined organics were dried with MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-38c95e4e1b9f4e528175183606fb1efa
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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