Donepezil → Donepezil methanesulfonate

HRID 1888019Notes

Reaction equation

HRID 1888019 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(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 702EthanolSolvent

Procedure

Methanesulfonic acid (1.3 ml, dissolved in 11 ml of absolute ethanol and 50 ml of dipropyl ether) is slowly added to a solution of Donepezil (3.79 g) in absolute ethanol (38 ml) with stirring at room temperature. The mixed solution is stirred at room temperature and the solid precipitated is filtered and dried 55° C. under vacuum to give the title compound. Melting point: 177.4° C.

Workup

  1. stirringThe mixed solution is stirred at room temperature
  2. customthe solid precipitated
  3. filtrationis filtered
  4. customdried 55° C. under vacuum

Sources & evidence

ORD record
ord-333450cece9244a5add40c532fbd94e7
Source dataset
uspto-grants-2013_08
Patent number
US08501779B2

Reaction notes

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