Donepezil → Donepezil methanesulfonate

HRID 1888014Notes

Reaction equation

HRID 1888014 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[CH2:19][CH:18]([CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:23][CH2:22]3)[C:16](=[O:17])[C:11]2=[CH:12][C:13]=1[O:14][CH3:15]>C(OCC)(=O)C>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[CH2:19][CH:18]([CH2:20][CH:21]3[CH2:22][CH2:23][N:24]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:25][CH2:26]3)[C:16](=[O:17])[C:11]2=[CH:12][C:13]=1[O:14][CH3:15].[S:2]([O-:5])(=[O:4])(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 3152DonepezilHCID 6395Methanesulfonic Acid

Product 1

HCID 131730793Donepezil methanesulfonate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonic acid (0.65 ml, dissolved in 35 ml of acetone) is slowly added to a solution of Donepezil (3.79 g) in ethyl acetate (70 ml) with stirring at room temperature. The solid precipitated is filtered and dried at 55° C. under vacuum to give the title compound. Melting point: 181.1° C.

Workup

  1. customThe solid precipitated
  2. filtrationis filtered
  3. customdried at 55° C. under vacuum

Sources & evidence

ORD record
ord-4ff8eeb5bbf9493cb392dec4c192947d
Source dataset
uspto-grants-2013_08
Patent number
US08501779B2

Reaction notes

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