1-(1-Naphthyl)piperazine → HCID 9907700, compound

HRID 2227244Notes

Reaction equation

HRID 2227244 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11](=[O:12])[CH:10]=[CH:9][C:8]([CH3:13])=[N:7]1.[C:14]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].ClCCl>C(#N)C.O>[C:14]1([N:24]2[CH2:29][CH2:28][N:27]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:11](=[O:12])[CH:10]=[CH:9][C:8]([CH3:13])=[N:7]3)[CH2:26][CH2:25]2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 13421-(1-Naphthyl)piperazineHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 13103481HCID 13103481, compound

Product 1

HCID 9907700HCID 9907700, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(4-bromobutyl)-6-methyl-3(2H)-pyridazinone (2.3 g, 9.5 mmol), 1-naphthylpiperazine (1.7 g, 8 mmol), K2CO3 (1.12 g, 8 mmol), and KI (10 mg) in acetonitrile (50 mL) was stirred at room temperature for 48 hours. Thereafter, the solvent was eliminated at reduced pressure and the residue 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 96:4), yielding 2-[4-(4-naphthylpiperazine-1-yl)-butyl]-6-methyl-3(2H)-pyridazinone (2.4 g). The product was dissolved in ethanol and by adding hydrochloric acid concentrated up to a 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. extractionthe aqueous phase was extracted with dichloromethane (twice)
  2. customThe organic extracts were collected
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe obtained residue was purified by flash chromatography (CH2Cl2/MeOH 96:4)

Sources & evidence

ORD record
ord-fd4fa1f144b74c50b4d36d4da5a501c8
Source dataset
uspto-grants-2002_07
Patent number
US06413966B1

Reaction notes

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