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

HRID 2416654
Notes
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Reaction equation

HRID 2416654 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 2756810tert-Butyl 3-methylpiperazine-1-carboxylate

Product 1

HCID 22633044Tert-butyl 3-methyl-4-(4-nitrophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

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

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate three times
  3. washThe combined organic layers were washed successively with water (twice) and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes