4-Methoxybiphenyl → HCID 22640158, compound

HRID 2415142Notes

Reaction equation

HRID 2415142 reaction equation
C([Li])CCC.[CH2:6]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CO[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1>CCCCCC.C1COCC1>[CH2:6]([N:13]1[CH2:18][CH2:17][N:16]([C:30]2[CH:31]=[CH:32][C:27]([C:24]3[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=3)=[CH:28][CH:29]=2)[CH2:15][CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 119434-MethoxybiphenylHCID 759941-BenzylpiperazineHCID 178418339Butyllithium

Product 1

HCID 22640158HCID 22640158, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

1.6 ml (0.05 mol) of butyllithium solution in n-hexane is added dropwise to a solution of 8.81 g (0.05 mol) of 1-benzylpiperazine in 50 ml of anhydrous THF under argon at 0° C. and stirred for one hour. Then 9.21 g (0.05 mol) of 4-methoxybiphenyl are added and the reaction mixture is refluxed for 12 hours. The solvent is then evaporated off, the residue is combined with 150 ml of 2 N hydrochloric acid followed by diethyl ether and the precipitate formed is filtered off. The precipitate is washed with diethyl ether, suspended in 20% sodium carbonate solution and extracted several times with dichloromethane. After drying over magnesium sulphate the solvent is removed and the residue is washed with ethyl acetate and diethyl ether.

Workup

  1. temperaturethe reaction mixture is refluxed for 12 hours
  2. customThe solvent is then evaporated off
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. washThe precipitate is washed with diethyl ether
  6. extractionextracted several times with dichloromethane
  7. dry with materialAfter drying over magnesium sulphate the solvent
  8. customis removed
  9. washthe residue is washed with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-6e64cfceef30490bafff1fdb7761382c
Source dataset
uspto-grants-2004_11
Patent number
US06818644B1

Reaction notes

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