Hydrochloric Acid → Donepezil Hydrochloride

HRID 1714123Notes

Reaction equation

HRID 1714123 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH2:14][CH:13]([CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:18][CH2:17]3)[C:11](=[O:12])[C:6]2=[CH:7][C:8]=1[O:9][CH3:10].[ClH:29]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH2:14][CH:13]([CH2:15][CH:16]3[CH2:17][CH2:18][N:19]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:20][CH2:21]3)[C:11](=[O:12])[C:6]2=[CH:7][C:8]=1[O:9][CH3:10].[ClH:29]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 3152Donepezil

Product 1

HCID 5741Donepezil HydrochlorideYield 96.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After completing the hydrogenation, the catalyst was removed from the reaction solution followed by concentration. To the concentrated residue, 700 ml of ethanol was added to obtain a solution. Subsequently, the solution was crystallized under stirring. Crystallized donepezil was filtered out, and then dried to obtain 76.6 g of donepezil. The obtained donepezil (76.5 g) was dissolved in 612 ml of ethanol. To the reaction solution, 23 g of concentrated hydrochloric acid was added under stirring, and the mixture was converted into its hydrochloride. The precipitated crystals were filtered out, and then dried to obtain 81.1 g of donepezil hydrochloride. The values of 1H-NMR were consistent with those of Example 3.

Workup

  1. filtrationThe precipitated crystals were filtered out
  2. customdried

Sources & evidence

ORD record
ord-d0573ed486d24b5d881e38bc66e674b3
Source dataset
uspto-grants-2010_09
Patent number
US07795438B2

Reaction notes

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