Benzyl Chloride → Donepezil

HRID 1645382Notes

Reaction equation

HRID 1645382 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH:7]([CH2:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH2:6]2.[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:22]([N:19]1[CH2:20][CH2:21][CH:16]([CH2:15][CH:7]2[CH2:6][C:5]3[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=3)[C:8]2=[O:14])[CH2:17][CH2:18]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 10446897Desbenzyl donepezil

Product 1

HCID 3152Donepezil

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4-[(5,6-Dimethoxy-1-indanon-2-yl)methyl]piperidine (4 g) was taken in acetone (60 ml). To which benzyl chloride (1.92 g), potassium carbonate (2.28 g) and a catalytic quantity of tetrabutylammonium iodide (TBAI) were added. The reaction mixture was heated at 60° C. and reaction was monitored on TLC. Solvent was removed by distillation after reaction completion and the residue was taken in water and extracted with ethyl acetate (100 ml). The organic extract was acidified with cone. HCl. The solvent was evaporated under vacuum to yield the salt as a residue. Yield: 5.14 g.

Workup

  1. customreaction
  2. customSolvent was removed by distillation
  3. customafter reaction completion
  4. extractionextracted with ethyl acetate (100 ml)
  5. extractionThe organic extract
  6. customThe solvent was evaporated under vacuum
  7. customto yield the salt as a residue

Sources & evidence

ORD record
ord-7fca73cdba884ff9b8ca8b216c86ef8c
Source dataset
uspto-grants-2012_02
Patent number
US08124783B2

Reaction notes

Loading…