Sesamol → N-Methylparoxetine

HRID 1836700Notes

Reaction equation

HRID 1836700 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:3]=2[O:2]1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH:37]2[CH2:43]Cl)=[CH:32][CH:31]=1>C(O)(C)C.CO>[CH3:42][N:39]1[CH2:38][C@@H:37]([CH2:43][O:10][C:7]2[CH:8]=[CH:9][C:3]3[O:2][CH2:1][O:5][C:4]=3[CH:6]=2)[C@H:36]([C:33]2[CH:32]=[CH:31][C:30]([F:29])=[CH:35][CH:34]=2)[CH2:41][CH2:40]1

Participants

5

Reactant 3

HCID 68289SesamolHCID 2723671Tetrabutylammonium HydroxideHCID 12997474HCID 12997474, compound

Product 1

HCID 10947895N-MethylparoxetineYield 76%

Reagents, catalysts & solvents 1

HCID 21255859Isopropanol methanolSolvent

Procedure

Sesamol (4.32 g, 31.2 mmol) was added to a solution of tetrabutylammonium hydroxide in isopropanol/methanol (0.1N, 342 mL), and the solvents were evaporated under vacuum to dryness. The residual tetrabutylammonium salt of sesamol was dissolved in acetonitrile (40 mL) and 4-(4-fluorophenyl)-3-chloromethyl-N-methyl-piperidine (CIPMA) (7.5 g, 31.2 mmol) was added. The reaction mixture was stirred with heating at reflux for 4 hours. After cooling, the reaction mixture was evaporated to dryness in vacuum and the residue was dissolved in toluene. The toluene solution was washed with 5% aq. sodium hydroxide and then with water. After drying with sodium sulfate and evaporation of the solvent in vacuum, N-methylparoxetine (8.1 grams) was obtained with yield 76%.

Workup

  1. customthe solvents were evaporated under vacuum to dryness
  2. dissolutionThe residual tetrabutylammonium salt of sesamol was dissolved in acetonitrile (40 mL)
  3. temperaturewith heating
  4. temperatureat reflux for 4 hours
  5. temperatureAfter cooling
  6. customthe reaction mixture was evaporated to dryness in vacuum
  7. dissolutionthe residue was dissolved in toluene
  8. washThe toluene solution was washed with 5% aq. sodium hydroxide
  9. dry with materialAfter drying with sodium sulfate and evaporation of the solvent in vacuum

Sources & evidence

ORD record
ord-726577665c01428a8d4d86e2586426fa
Source dataset
uspto-grants-2004_08
Patent number
US06777554B2

Reaction notes

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