Piperazine → HCID 58585369, compound

HRID 2252280Notes

Reaction equation

HRID 2252280 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]([Cl:15])=[C:11](Cl)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>CN(C)C=O>[Cl:15][C:12]1[C:13](=[O:14])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[CH:10][C:11]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 7794024,5-Dichloro-2-(4-chlorophenyl)-3(2H)-pyridazinone

Product 1

HCID 58585369HCID 58585369, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

55.1 g (200 mmol) of 2-(4-chlorophenyl)-4,5-dichlorpyridazin-3-one are introduced with 41.6 ml (300 mmol) of triethylamine in 400 ml of dimethylformamide. 137.82 g (1600 mmol) of piperazine are added, and the mixture is stirred at 80° C. overnight. The reaction mixture is cooled and then concentrated under high vacuum. The residue is taken up in dichloromethane and washed twice with water, dried over magnesium sulfate and concentrated. The product is isolated by chromatography (gradient: dichloromethane/methanol from 95:5 to 9:1) on silica gel and subsequent crystallization with ether.

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated under high vacuum
  3. washwashed twice with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe product is isolated by chromatography (gradient: dichloromethane/methanol from 95:5 to 9:1) on silica gel and subsequent crystallization with ether

Sources & evidence

ORD record
ord-b4afcbf2ba134864a016e95d442dfcd4
Source dataset
uspto-grants-2008_01
Patent number
US07320977B2

Reaction notes

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