Ammonium Chloride → 3-(4-Cyclopropyl-piperazin-1-yl)-6-(3-nitro-phenyl)-pyridazine

HRID 1887167Notes

Reaction equation

HRID 1887167 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)=[CH:6][CH:7]=1.[CH:17]1([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH2:19][CH2:18]1.[NH4+].[Cl-]>CCCCO>[CH:17]1([N:20]2[CH2:25][CH2:24][N:23]([C:2]3[N:3]=[N:4][C:5]([C:8]4[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=4)=[CH:6][CH:7]=3)[CH2:22][CH2:21]2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 47420041-CyclopropylpiperazineHCID 122575043-Chloro-6-(3-nitrophenyl)pyridazine

Product 1

HCID 580066013-(4-Cyclopropyl-piperazin-1-yl)-6-(3-nitro-phenyl)-pyridazineYield 5.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-chloro-6-(3-nitro-phenyl)-pyridazine (10.0 g, 424 mmol) in n-BuOH (150 mL) was added 1-cyclopropyl-piperazine (8.55 g, 678 mmol) and NH4Cl (2.27 g, 424 mmol) and the mixture was stirred for 48 h at 80° C. The solvent was removed under reduced pressure, and the residue was diluted with water. After alkalization with ammonia, the mixture was extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated to give 7.2 g of crude 3-(4-cyclopropyl-piperazin-1-yl)-6-(3-nitro-phenyl)-pyridazine.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionAfter alkalization with ammonia, the mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e143fca1a6ed4ceb880376a1ed48ce70
Source dataset
uspto-grants-2013_08
Patent number
US08501739B2

Reaction notes

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