1-Isopropylpiperazine → 1-Isopropyl-4-(5-nitro-pyridin-2-yl)-piperazine

HRID 2066726Notes

Reaction equation

HRID 2066726 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].Cl[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1>C(Cl)Cl.C(Cl)Cl.O>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 780131-IsopropylpiperazineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 339957181-Isopropyl-4-(5-nitro-pyridin-2-yl)-piperazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21908982Water methylene chlorideSolvent

Procedure

N-Isopropylpiperazine (1.8 mL, 12.7 mmol, 2 equiv) is added to a cold (5° C.) mixture of 2-chloro-5-nitropyridine (1 g, 6.3 mmol) in DCM (5 mL). The reaction mixture is allowed to warm to RT, stirred for 16 h, diluted with DCM/H2O and extracted with DCM. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated to provide the title compound as a yellow solid: ES-MS: 251.2 [MH]+; tR=2.20 min (system 1).

Workup

  1. extractionextracted with DCM
  2. washThe organic phase is washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-97196213fe1246e79d40e6326d24db11
Source dataset
uspto-grants-2012_10
Patent number
US08293746B2

Reaction notes

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