Piperazine → 3-Pyridazinamine, 6-(4-methyl-1-piperazinyl)-

HRID 2236532Notes

Reaction equation

HRID 2236532 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.Cl.Cl[C:11]1C=CC=NC=1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:11][N:17]1[CH2:22][CH2:21][N:20]([C:5]2[N:4]=[N:3][C:2]([NH2:1])=[CH:7][CH:6]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 4

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 216436-Amino-3-chloropyridazineHCID 184065973-Chloropyridine--hydrogen chloride (1/1)

Product 1

HCID 203168163-Pyridazinamine, 6-(4-methyl-1-piperazinyl)-Yield 53.6%

Procedure

An amount of 1.0 g (7.72 mmol) of 3-amino-6-chloropyridazine, 5-chloro pyridine hydrogen chloride (4.46 g, 38.6 mmol), and piperazine (5.1 mL, 72 mmol) were placed in a pre-heated oil bath at 165-170° C. for 4 hours. After cooling, the mixture is basified with saturated potassium carbonate, extracted 3× with ethyl acetate and dried over magnesium sulfate. The oily residue is purified by column chromatography to give a brown solid 800 mg (53% yield). MS (ESI) m/z 194.3 (M+1)+

Workup

  1. temperatureAfter cooling
  2. extractionextracted 3× with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customThe oily residue is purified by column chromatography

Sources & evidence

ORD record
ord-094ec649dfa144e792abdc6e816c4e94
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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