Donepezil → Donepezil methanesulfonate

HRID 1888018

Reaction equation

HRID 1888018 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(OCCC)CC>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

5

Reactant 3

HCID 3152DonepezilHCID 6395Methanesulfonic AcidHCID 8114Propyl ether

Product 1

HCID 131730793Donepezil methanesulfonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methanesulfonic acid (1.3 ml, dissolved in 11 ml of absolute ethanol) is slowly added to a solution of Donepezil (3.79 g) in absolute ethanol (38 ml) with stirring at room temperature, and 50 ml of dipropyl ether is added. The solid precipitated is filtered and dried at 55° C. under vacuum to give the title compound. Melting point: 180.3° C.

Workup

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

Sources & evidence

ORD record
ord-2dc43549994e4f18bcf31875780ac882
Source dataset
uspto-grants-2013_08
Patent number
US08501779B2

Linked notes

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