Water → Tert-butyl 3-methyl-4-(4-nitrophenyl)piperazine-1-carboxylate

HRID 2416654Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (±)-tert-butyl 3-methylpiperazine-1-carboxylate (1.5 g), 1-fluoro-4-nitrobenzene (1.06 g) and potassium carbonate (2.07 g) in dimethyl sulfoxide (15 ml) was stirred at 120° C. for 15 hours. The reaction mixture was cooled to room temperature and poured into water (30 ml). The mixture was extracted with ethyl acetate three times. The combined organic layers were washed successively with water (twice) and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 2:1) to give the title compound as a white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionThe mixture was extracted with ethyl acetate three times
washThe combined organic layers were washed successively with water (twice) and brine
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate 2:1)

Sources & evidence

ORD record: ord-ccc82224581841139373a20a59be8034
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825200B1

Reaction notes

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