3,6-Dichloropyridazine → 3-[4-(6-Chloropyridazin-3-yl)piperazin-1-yl]propane-1,2-diol

HRID 231763Notes

Reaction equation

HRID 231763 reaction equation
[OH:1][CH:2]([CH2:10][OH:11])[CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[Cl:12][C:13]1[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=1>C(O)(C)C>[Cl:12][C:13]1[N:14]=[N:15][C:16]([N:7]2[CH2:8][CH2:9][N:4]([CH2:3][CH:2]([OH:1])[CH2:10][OH:11])[CH2:5][CH2:6]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 673313,6-DichloropyridazineHCID 1110023-(Piperazin-1-yl)propane-1,2-diol

Product 1

HCID 200320123-[4-(6-Chloropyridazin-3-yl)piperazin-1-yl]propane-1,2-diol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Grams 32 of 1-(2,3-dihydroxypropyl)piperazine and 15 g of 3,6-dichloropyridazine in 700 ml isopropanol were refluxed for 24 hours. The reaction mixture was settled, the solid undissolvable removed and the solution evaporated to dryness. The so obtained residue was purified on column eluting with chloroform:methanol (9:1). Grams 2.1 of 3-[4-(6-chloropyridazin-3-yl)piperazin-1-yl]propane-1,2-diol, which, recrystallized from acetone, melted at 126°-128° C.

Workup

  1. customthe solid undissolvable removed
  2. customthe solution evaporated to dryness
  3. customThe so obtained residue
  4. customwas purified on column
  5. washeluting with chloroform:methanol (9:1)
  6. customGrams 2.1 of 3-[4-(6-chloropyridazin-3-yl)piperazin-1-yl]propane-1,2-diol, which, recrystallized from acetone, melted at 126°-128° C.

Sources & evidence

ORD record
ord-09a899ee5eb7470b9150cd42a19f1862
Source dataset
uspto-grants-1989_07
Patent number
US04849422

Reaction notes

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