Triethylamine → [4-(4-Hydroxyphenyl)-1-piperazinyl]-1-naphthalenylmethanone

HRID 1434587Notes

Reaction equation

HRID 1434587 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:21]1([C:31](Cl)=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>ClCCl>[C:21]1([C:31]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=3)[CH2:6][CH2:5]2)=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701461-Naphthalenecarbonyl chlorideHCID 92467p-(1-Piperazinyl)phenol

Product 1

HCID 57935728[4-(4-Hydroxyphenyl)-1-piperazinyl]-1-naphthalenylmethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring mixture of 4-(1-piperazinyl)phenol (5.54 g) and triethylamine (10.83 ml) in dichloromethane (140 ml) was added dropwise, 1-naphthalenecarbonyl chloride (9.83 ml). The resulting reaction mixture was stirred under a nitrogen atmosphere for 3 h. The mixture was partitioned between dichloromethane and water and the organic phase was washed with saturated brine, dried (MgSO4) and evaporated to dryness. The residue was suspended in 6:4 tetrahydrofuran-methanol (370 ml) and treated with a saturated solution of potassium carbonate in methanol (45 ml). The mixture was stirred at room temperature under a nitrogen atmosphere for 20 h. The solvent was evaporated and the residue was partitioned between dichloromethane and water. The organic phase was washed with saturated brine, dried (MgSO4) and evaporated to give an oil (15.5 g), part of which (14.5 g) was purified by chromatography on a silica SPE bond elut cartridge eluting with 10% -80% ethyl acetate-cyclohexane gradient to give the title compound (8.9 g). LCMS RT=2.97 min.

Workup

  1. additionwas added dropwise
  2. customThe resulting reaction mixture
  3. customThe mixture was partitioned between dichloromethane and water
  4. washthe organic phase was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness
  7. additiontreated with a saturated solution of potassium carbonate in methanol (45 ml)
  8. stirringThe mixture was stirred at room temperature under a nitrogen atmosphere for 20 h
  9. customThe solvent was evaporated
  10. customthe residue was partitioned between dichloromethane and water
  11. washThe organic phase was washed with saturated brine
  12. dry with materialdried (MgSO4)
  13. customevaporated

Sources & evidence

ORD record
ord-5ef9e2c6396c4b9da9b2d7c38c43d8d3
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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