1-(1-Naphthyl)piperazine → HCID 15887922, compound

HRID 2227246Notes

Reaction equation

HRID 2227246 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:5]1.[C:17]1([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].ClCCl>C(#N)C.O>[C:17]1([N:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][N:4]3[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:5]3)[CH2:29][CH2:28]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 13421-(1-Naphthyl)piperazineHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 12554433HCID 12554433, compound

Product 1

HCID 15887922HCID 15887922, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(2-chloroethyl)-6-phenyl-3(2H)-pyridazinone (1.9 g, 7.5 mmol), 1-naphthylpiperazine (1.7 g, 8 mmol), K2CO3 (1.12 g, 8 mmol) and KI (10 mg) in acetonitrile (50 mL) was refluxed for 7 hours. When heating, was over, the solvent was eliminated at reduced pressure and distributed between dichloromethane and water; the aqueous phase was extracted with dichloromethane (twice). The organic extracts were collected, dried over anhydrous Na2SO4 and concentrated to dryness. The obtained residue was purified by flash chromatography (CH2Cl2/MeOH 97:3) yielding 2-[2-(4-naphthylpiperazine-1-yl)-ethyl]-6-phenyl-3(2H)-pyridazinone (2.1 g). The product was dissolved in ethanol and by adding hydrochloric acid concentrated up to pH=1 yielded a white solid, which was re-crystallised in methanol, yielding the hydrochloride of the title compound, presenting a M.P. higher than 260° C.

Workup

  1. temperaturewas refluxed for 7 hours
  2. temperatureWhen heating
  3. extractionthe aqueous phase was extracted with dichloromethane (twice)
  4. customThe organic extracts were collected
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe obtained residue was purified by flash chromatography (CH2Cl2/MeOH 97:3)

Sources & evidence

ORD record
ord-f311ad47b6a94c359d8a359abbdebeed
Source dataset
uspto-grants-2002_07
Patent number
US06413966B1

Reaction notes

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