6-Amino-3-chloropyridazine → 6-(4-Benzylpiperazin-1-yl)pyridazin-3-ylamine

HRID 80717

Reaction equation

HRID 80717 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:14][C:15]1[N:16]=[N:17][C:18](Cl)=[CH:19][CH:20]=1>C(=O)(O)[O-].[Na+]>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:18]2[N:17]=[N:16][C:15]([NH2:14])=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 759941-Benzylpiperazine

Product 1

HCID 593677126-(4-Benzylpiperazin-1-yl)pyridazin-3-ylamineYield 82.2%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

48.9 g (278 mmol) of 1-benzylpiperazine and 12.0 g (92.6 mmol) of 3-amino-6-chloropyridazine are heated at 160° C. for 1 hour. The brown oil obtained is poured into 500 mL of aqueous sodium bicarbonate solution and the product is extracted with dichloromethane. The organic phase is dried and then concentrated under reduced pressure. The oil obtained is triturated in diethyl ether, and 20.5 g of a solid are isolated after filtering off and drying.

Workup

  1. customThe brown oil obtained
  2. extractionthe product is extracted with dichloromethane
  3. customThe organic phase is dried
  4. concentrationconcentrated under reduced pressure
  5. customThe oil obtained
  6. customis triturated in diethyl ether

Sources & evidence

ORD record
ord-365f660cdcd04b8c95be9d01d77f0cb0
Source dataset
uspto-grants-2014_09
Patent number
US08846676B2

Linked notes

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