3-Chloro-6-(1-piperazinyl)pyridazine → 3-(1-Methylethoxy)-6-(1-piperazinyl)pyridazine

HRID 1979948Notes

Reaction equation

HRID 1979948 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[CH3:14][CH:15]([CH3:17])[O-:16].[Na+].[Na]>C(O)(C)C>[CH:15]([O:16][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1)([CH3:17])[CH3:14]

Participants

5

Reactant 3

HCID 52949263-Chloro-6-(1-piperazinyl)pyridazineHCID 5360545SodiumHCID 109204432-Propanol, sodium salt (1:1)

Product 1

HCID 138695653-(1-Methylethoxy)-6-(1-piperazinyl)pyridazine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-Chloro-6-piperazinopyridazine (4.0 g) [J. Med. Chem., 5, 541 (1963)] and sodium isopropoxide, prepared by addition of sodium (0.7 g) to dry isopropanol (70 ml), were heated in a bomb at 130°-140° C. for 10 hours. The solvent was evaporated in vacuo, the residue taken up in methylene chloride (300 ml) and the resulting solution washed with water (2×50 ml). The organic extract was dried (Na2SO4) and evaporated in vacuo to give 3-isopropoxy-6-piperazinopyridazine (3.3 g). A sample in ethyl acetate, was converted to the maleate salt by treatment with maleic acid in ethyl acetate. The resulting solid was re-crystallized from ethanol, m.p. 144°-145° C.

Workup

  1. temperaturewere heated in a bomb at 130°-140° C. for 10 hours
  2. customThe solvent was evaporated in vacuo
  3. washthe resulting solution washed with water (2×50 ml)
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-498d7f0b852e45af9f60e9f22bc1dfad
Source dataset
uspto-grants-1984_11
Patent number
US04483859

Reaction notes

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