Piperazine → 1-(3-Nitropyridin-2-yl)piperazine

HRID 490210Notes

Reaction equation

HRID 490210 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C(O)(C)C>[N+:8]([C:7]1[C:2]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 37788341-(3-Nitropyridin-2-yl)piperazine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 2-chloro-3-nitropyridine (10.05 g, 63.39 mmol) in isopropyl alcohol (350 mL) at room temperature was added piperazine (27.48 g, 319.0 mmol) in one portion. After 2 hours, the solvent was removed under reduced pressure and the residue partitioned between water and dichloromethane. The organic phase was dried (sodium sulfate), filtered and concentrated to a bright yellow solid. This material was used without further purification. 1H NMR (300 MHz, CDCl3) δ 1.74 (s, 1H), 2.98 (m, 4H), 3.43 (m, 4H), 6.73 (dd, 1H, J=8.1, 4.8 Hz), 8.11 (dd, 1H, J=8.1, 1.7 Hz), 8.32 (dd, 1H, J=4.4, 1.7 Hz); MS (DCI/NH3) m/e 209 (M+H)+.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue partitioned between water and dichloromethane
  3. dry with materialThe organic phase was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated to a bright yellow solid
  6. customThis material was used without further purification

Sources & evidence

ORD record
ord-e54b0f3668714d4d931b337124fde7a5
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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