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

HRID 515561Notes

Reaction equation

HRID 515561 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-422f40e93e8b4c719c9d4fca244835c3
Source dataset
uspto-grants-2015_08
Patent number
US09108971B2

Reaction notes

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