Water → Tert-butyl 4-[4-(methoxycarbonyl)-2-nitrophenyl]piperazine-1-carboxylate

HRID 1038528Notes

Reaction equation

HRID 1038528 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([N:18]2[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]2)=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 66598073Tert-butyl 4-[4-(methoxycarbonyl)-2-nitrophenyl]piperazine-1-carboxylateYield 104.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-fluoro-3-nitrobenzoate (2.50 g, 12.6 mmol) in tetrahydrofuran (75 mL), tert-butyl piperazine-1-carboxylate (4.67 g, 25.2 mmol) and potassium carbonate (4.34 g, 25.2 mmol) were added sequentially under ice-cold conditions, and the mixture was stirred at room temperature for 1 hour. The reaction solution was added water under ice-cold conditions, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (ethyl acetate). The title compound (4.83 g (yield 100%)) was obtained as a yellow crystal.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica-gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-4b95f3b9df3b4ac9a5e2f61909f160ff
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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