p-Anisoyl chloride → HCID 23361088, compound

HRID 232893Notes

Reaction equation

HRID 232893 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][C:4]2([CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8]2)[CH2:3]1.[CH3:17][O:18][C:19]1[CH:27]=[CH:26]C(C(Cl)=O)=[CH:21][CH:20]=1.[C:28](OCC)(=O)C>C(=O)([O-])[O-].[K+].[K+]>[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:1]([N:2]2[CH2:7][CH2:6][N:5]([CH3:28])[C:4]3([CH2:16][CH2:15][C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH2:8]3)[CH2:3]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8857Ethyl AcetateHCID 23361041HCID 23361041, compound

Product 1

HCID 23361088HCID 23361088, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

1'-methylspiro[tetralin-2,3'-piperazine] (50 mg, 0.23 mmol) was dissolved in ethyl acetate (4 ml)-saturated aqueous potassium carbonate solution (4 ml). While the solution was vigorously stirred, p-methoxybenzoyl chloride (51 mg, 0.3 mmol) was added. After the organic layer was separated, the solvent was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography for elution with n-hexane-ethyl acetate (9:1) to yield 60 mg (74%) of the title compound as a crude crystal.

Workup

  1. customAfter the organic layer was separated
  2. concentrationthe solvent was concentrated under reduced pressure
  3. washThe obtained residue was subjected to silica gel column chromatography for elution with n-hexane-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-d112b9d32ac6418a977d709380021ccf
Source dataset
uspto-grants-1997_01
Patent number
US05591849

Reaction notes

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