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

HRID 1253592Notes

Reaction equation

HRID 1253592 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 3

HCID 216436-Amino-3-chloropyridazineHCID 759941-BenzylpiperazineHCID 516892Sodium Bicarbonate

Product 1

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

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 an aqueous solution of sodium bicarbonate 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 filtration 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-652ae7d1d3a640acb63c7745c0fe9c50
Source dataset
uspto-grants-2013_06
Patent number
US08455491B2

Reaction notes

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