Triethylamine → 1-Tert-butyl-4-(4-nitrophenyl)piperazine

HRID 875144Notes

Reaction equation

HRID 875144 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.Br.Br.[C:13]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>C(#N)C.O>[C:13]([N:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 219063541-Tert-butylpiperazine dihydrobromide

Product 1

HCID 574441581-Tert-butyl-4-(4-nitrophenyl)piperazineYield 272.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 800 mg (5.67 mmol) of 1-fluoro-4-nitrobenzene, 2.07 g (1.2 mmol) of 1-tert-butylpiperazine dihydrobromide and 3.2 mL (20.41 mmol) of triethylamine, in 22 mL of acetonitrile, was refluxed for 10 hours. The mixture was cooled to room temperature, diluted with water and extracted with dichloromethane. The organic layer was washed with water and brine, dried over Na2SO4 and evaporated. Purification by flash chromatography (eluant dichloromethane/methanol 7/3) yielded 860 mg of the title compound as yellow solid.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customPurification by flash chromatography (eluant dichloromethane/methanol 7/3)

Sources & evidence

ORD record
ord-a5c1639a68a54419b752d0c1d78e1da5
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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