Piperazine → 1-(5-Nitropyridin-2-yl)piperazine

HRID 892995Notes

Reaction equation

HRID 892995 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 29287991-(5-Nitropyridin-2-yl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-Chloro-5-nitropyridine (25 g) is dissolved in acetonitrile (150 ml) and the mixture is added dropwise over 30 min to a stirred suspension of piperizine (61.3 g) and potassium carbonate (26.2 g) in acetonitrile (550 ml). The reaction mixture is stirred at 20°-25° for 16 hr. The solvent is removed on a rotary evaporator and the residue is diluted with methylene chloride/water. The organic layer is separated and washed with water (twice) and saline, dried over potassium carbonate and concentrated to give 1-(5-nitro-2-pyridinyl)-piperazine, IR 3338, 3102, 3068, 1603, 1570, 1482, 1347, 1340, 1320, 1306 and 1253 cm-1.

Workup

  1. customThe solvent is removed on a rotary evaporator
  2. additionthe residue is diluted with methylene chloride/water
  3. customThe organic layer is separated
  4. washwashed with water (twice) and saline
  5. dry with materialdried over potassium carbonate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-55249fe3139747c6a0f3d792ee471bc4
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

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