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

HRID 2391782Notes

Reaction equation

HRID 2391782 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)-piperazine

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 he 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-7b8ff1ebddd94ac5825eda769ab314c3
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

Loading…