Hydrochloric Acid → Donepezil Hydrochloride

HRID 1602838Notes

Reaction equation

HRID 1602838 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].CC(OC)(C)C>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3152DonepezilHCID 15413tert-Butyl methyl ether

Product 1

HCID 5741Donepezil Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

2.0 g of Donepezil was dissolved in 20 ml of ethanol under heating at 40° C. The solution was cooled to room temperature in an iced water bath. Hydrogen chloride gas was blown hereinto at 24° C. inner temperature, until the atmosphere turns acidic. After stirring for 10 minutes, 50 ml of TBME was added. It continued stirring over night at room temperature. Filtration of the separated crystals followed by drying afforded 2.11 g of the title compound. (water content: 0.07%)

Workup

  1. temperatureThe solution was cooled to room temperature in an iced water bath
  2. customwas blown hereinto at 24° C. inner temperature, until the atmosphere
  3. stirringIt continued stirring over night at room temperature
  4. filtrationFiltration of the separated crystals
  5. customby drying

Sources & evidence

ORD record
ord-01b0ec96f49a47e3bcf6b7fd372557e2
Source dataset
uspto-grants-1999_11
Patent number
US05985864

Reaction notes

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