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

HRID 43069Notes

Reaction equation

HRID 43069 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.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)-piperazineYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1-Isopropylpiperazine (1.8 mL, 12.7 mmol, 2 equiv) was added to a cold (5° C.) solution of 2-chloro-5-nitropyridine (1 g, 6.3 mmol,) in DCM (5 mL). The reaction mixture was allowed to warm to rt, stirred for 16 h, diluted with DCM and H2O. The aqueous layer was separated and extracted with DCM. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated to provide 1.58 g of the title compound as a yellow solid: ESI-MS: 251.2 [M+H]+; tR=2.20 min.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c6fcd5313b494ed990cc35f96102f438
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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