Piperazine → HCID 20785294, compound

HRID 1775361Notes

Reaction equation

HRID 1775361 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>N1C=CC=CC=1>[N:11]1([C:2]2[CH:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][N:3]=2)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 131452551-(2-Chloropyridin-4-yl)ethan-1-one

Product 1

HCID 20785294HCID 20785294, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(2-Chloro-4-pyridyl)ethanone (156 mg, 1 mmol), piperazine (861 mg, 10 mmol) and pyridine (5 ml) were placed in a Radley vial and heated at reflux overnight. The mixture was concentrated under reduced pressure to dryness, the residue was mixed with toluene and evaporated under reduced pressure to remove excess of piperazine. The last step was repeated several times. The residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile) to yield 51 mg of a solid (0.21 mmol, yield 21%) MS (multi-mode) m/z=206.2 [M+1]+.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated under reduced pressure to dryness
  4. additionthe residue was mixed with toluene
  5. customevaporated under reduced pressure
  6. customto remove excess of piperazine
  7. customThe residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile)

Sources & evidence

ORD record
ord-bd85cb7d8612487385833b7ff2570745
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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