Allyl chloride → 4-[4-(4-Pyridyl)piperazin-1-yl]phenol allyl ether

HRID 1291897Notes

Reaction equation

HRID 1291897 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH2:22](Cl)[CH:23]=[CH2:24]>CN(C=O)C>[CH2:24]([O:21][C:18]1[CH:19]=[CH:20][C:15]([N:12]2[CH2:11][CH2:10][N:9]([C:6]3[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=3)[CH2:14][CH2:13]2)=[CH:16][CH:17]=1)[CH:23]=[CH2:22]

Participants

5

Reactant 3

HCID 7850Allyl chlorideHCID 24758Sodium hydrideHCID 149869034-(4-(4-Pyridyl)piperazin-1-yl)phenol

Product 1

HCID 571157974-[4-(4-Pyridyl)piperazin-1-yl]phenol allyl etherYield 85.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.4 g) was added to a stirred suspension of 4-[4-(4-pyridyl)piperazin-1-yl]phenol (2.55 g) in DMF (25 ml) and the mixture stirred for 20 minutes at room temperature. Allyl chloride (0.756 g) was added dropwise and stirring continued for 20 hours. Ice-water (75 ml) was added and the mixture extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried (MgSO4) and evaporated. The residue was triturated with hexane and filtered to give 4-[4-(4-pyridyl)piperazin-1-yl]phenol allyl ether (2.5 g) as a solid; NMR(d6DMSO) δ 8.18(2H,dd), 6.8-7.0(6H,m), 5.92-6.13(1H,m), 5.2-5.45(2H,m), 4.5(2H,m), 3.45(4H,m), 3.11(4H,m).

Workup

  1. stirringstirring
  2. waitcontinued for 20 hours
  3. extractionthe mixture extracted three times with ethyl acetate
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was triturated with hexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-386d20dea49f48e194d44e72f8c54844
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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