Piperazine → 5,7-Dimethyl-2-(1-piperazinyl)benzoxazole

HRID 984074Notes

Reaction equation

HRID 984074 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]2[O:9][C:8](S)=[N:7][C:6]=2[CH:11]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>[N+](C)([O-])=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]2[O:9][C:8]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:7][C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 178424102HCID 178424102, compound

Product 1

HCID 116227525,7-Dimethyl-2-(1-piperazinyl)benzoxazole

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A 50 mg portion of 5,7-dimethyl-2-mercaptobenzoxazole was dissolved in 5 ml of nitromethane, and the solution was mixed with 240 mg of piperazine and heated under reflux for 12 hours. The solvent was concentrated under a reduced pressure, and the residual oily matter was mixed with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate, and then the solvent was evaporated under a reduced pressure. Thereafter, the thus obtained mixture was purified by a silica gel column chromatography (chloroform:methanol=20:1) to obtain the title compound (35 mg) in white color.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe solvent was concentrated under a reduced pressure
  4. additionthe residual oily matter was mixed with saturated sodium bicarbonate aqueous solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. customthe solvent was evaporated under a reduced pressure
  9. customThereafter, the thus obtained mixture was purified by a silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-ab1dce626c9847afb2524613fcf72cda
Source dataset
uspto-grants-2005_03
Patent number
US06867226B2

Reaction notes

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