Water → HCID 2967785, compound

HRID 271559Notes

Reaction equation

HRID 271559 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[CH3:26].O>C(#N)C>[CH3:26][C:18]1[CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:17]=1[N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 81531Diisopropylethylamine

Product 1

HCID 2967785HCID 2967785, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of piperazine (3.0 mmol), N,N-diisopropylethylamine (6.0 mmol), and 2-fluoro-5-nitrotoluene (7.5 mmol) in acetonitrile are stirred at 50° C. for 3 h and then 100° C. for 9.5 h, and poured into water. The mixture is extracted with AcOEt. The organic layer is washed with water, dried over magnesium sulfate, and concentrated. The crude product is purified by silica gel column chromatography to give the product in 85% yield.

Workup

  1. wait100° C. for 9.5 h
  2. extractionThe mixture is extracted with AcOEt
  3. washThe organic layer is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified by silica gel column chromatography
  7. customto give the product in 85% yield

Sources & evidence

ORD record
ord-bcef5b1a55d54000bb5ed829e6ecf442
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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