1-Piperonylpiperazine → HCID 22047820, compound

HRID 884164Notes

Reaction equation

HRID 884164 reaction equation
C1([O:7][C:8](=[O:34])NC2C=CC(OC3C=CC(NC(=O)C4C=CC(Cl)=C(Cl)C=4)=CN=3)=CC=2)C=CC=CC=1.[CH2:35]([N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)[C:36]1[CH:44]=[CH:43][C:42]2[O:41][CH2:40][O:39][C:38]=2[CH:37]=1>CN(C=O)C>[CH2:35]([N:45]1[CH2:50][CH2:49][N:48]([C:8]([OH:34])=[O:7])[CH2:47][CH2:46]1)[C:36]1[CH:44]=[CH:43][C:42]2[O:41][CH2:40][O:39][C:38]=2[CH:37]=1

Participants

4

Reactant 2

HCID 944261-PiperonylpiperazineHCID 68525769HCID 68525769, compound

Product 1

HCID 22047820HCID 22047820, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of {4-[5-(3,4-dichlorobenzoyl-amino)pyridin-2-yloxy]phenyl}-carbamic acid phenyl ester (320 mg, 0.65 mmol) in DMF (4 mL) was added 1-piperonylpiperazine (285 mg, 1.29 mmol), and the resulting solution was stirred for 17 hours at room temperature. This reaction solution was concentrated under reduced pressure. Water was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was then purified by silica gel column chromatography (dichloromethane:methanol=25:1). The obtained residue was dissolved in a mixed solvent of ethanol-ethyl acetate. To the resulting solution was added a solution of 4 N hydrogen chloride in ethyl acetate to bring the pH to 3. The precipitated white powder was then filtered off and washed with ethanol, to thereby yield 330 mg of the title compound.

Workup

  1. concentrationThis reaction solution was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was then purified by silica gel column chromatography (dichloromethane:methanol=25:1)
  8. dissolutionThe obtained residue was dissolved in a mixed solvent of ethanol-ethyl acetate
  9. additionTo the resulting solution was added a solution of 4 N hydrogen chloride in ethyl acetate
  10. filtrationThe precipitated white powder was then filtered off
  11. washwashed with ethanol

Sources & evidence

ORD record
ord-bdc85e9418cf4afa894449e29d5545a4
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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