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Donepezil
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Name

Donepezil

 EINECS 601-651-9
CAS No. 120014-06-4 Density 1.141 g/cm3
PSA 38.77000 LogP 4.29900
Solubility 2.931 mg/L in water Melting Point 207 ºC
Formula C24H29NO3 Boiling Point 527.9 ºC at 760 mmHg
Molecular Weight 379.499 Flash Point 273.1 ºC
Transport Information N/A Appearance white or almost white crystal powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 120014-06-4 (2-[(1-Benzyl-4-piperidyl)methyl]-5,6-dimethoxy-2,3-dihydroinden-1-one) Hazard Symbols IrritantXi
Synonyms

1-Benzyl-4-[(5,6-dimethoxy-1-oxoindan-2-yl)methyl]piperidine;Donepezil base;

Article Data 68

Donepezil Synthetic route

ethyl acetate thrice

ethyl acetate thrice

(±)-2-[(1-benzylpyridin-1-ium-4-yl)methyl]-5,6-dimethoxy-indan-1-one bromide

120014-06-4

donepezil

Conditions
ConditionsYield
In methanol99%

donepezil hydrochloride

120014-06-4

donepezil

Conditions
ConditionsYield
With sodium hydroxide In water; ethyl acetate for 0.5h; pH=11.7; Reagent/catalyst; Solvent; pH-value;97.5%
With sodium hydrogencarbonate In water; toluene at 60 - 65℃; for 0.5h; Purification / work up;
Stage #1: donepezil hydrochloride With sodium hydrogencarbonate In water; toluene at 60 - 65℃; for 0.75h;
Stage #2: In water; isopropyl alcohol at 10 - 70℃; for 10h; Product distribution / selectivity;

2,3-dihydro-5,6-dimethoxy-2-((piperidin-4-yl)methyl)inden-1-one p-toluenesulfonic acid salt

100-39-0

benzyl bromide

120014-06-4

donepezil

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Product distribution / selectivity;96%
100-39-0

benzyl bromide

120014-30-4

debenzyldonepezil

120014-06-4

donepezil

Conditions
ConditionsYield
With sodium carbonate In ethanol at 50 - 60℃; for 6h;92.3%
With triethylamine In dichloromethane for 4h; Heating / reflux;
Stage #1: benzyl bromide; debenzyldonepezil With tetrabutylammomium bromide; potassium carbonate In dichloromethane; water at 20℃;
Stage #2: With hydrogenchloride In methanol
259170-03-1

2-(3,4-dimethoxybenzyl)-3-(N-benzyl-4-piperidine)propionic acid

120014-06-4

donepezil

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; trifluoroacetic anhydride In dichloromethane at 24 - 28℃; Inert atmosphere; chemoselective reaction;90%

(E)-2-((1-benzylpiperidine-4-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

120014-06-4

donepezil

Conditions
ConditionsYield
With sodium dithionite; tetrabutylammomium bromide; sodium hydrogencarbonate In water; ethyl acetate88%
With sodium dithionite; tetrabutylammomium bromide; water; sodium hydrogencarbonate In ethyl acetate at 65℃; for 0.5h; Solvent; Temperature; Time;88%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 760.051 Torr; for 12h;78%
With hydrogen; palladium carbon In methanol at 20℃; under 760.051 Torr; for 2h;31 g
With hydrogen In tetrahydrofuran; water; isopropyl alcohol at 25℃; under 760.051 Torr; for 20h; Catalytic behavior; Flow reactor; chemoselective reaction;95 %Spectr.
2107-69-9

5,6-dimethoxy-1-indanone

22065-85-6

1-benzyl-4-formylpiperidine

120014-06-4

donepezil

Conditions
ConditionsYield
With aluminum oxide; Pt/Al2O3 In tetrahydrofuran; ethanol; water; isopropyl alcohol at 45 - 55℃; for 7h; Temperature; Solvent; Reagent/catalyst; Aldol Condensation;88%
Multi-step reaction with 2 steps
1: sodium methylate / tetrahydrofuran
2: palladium 10% on activated carbon; hydrogenchloride / ethanol; water
View Scheme
120012-04-6

1-benzyl-4-[(5,6-dimethoxy-1-indanol)-2-yl]methylpiperidine

120014-06-4

donepezil

Conditions
ConditionsYield
With tert.-butylhydroperoxide; tetrabutylammomium bromide In decane; benzene at 40℃; for 24h; Sealed tube; chemoselective reaction;85%
2107-69-9

5,6-dimethoxy-1-indanone

67686-01-5

1-benzyl-4-piperidinemethanol

120014-06-4

donepezil

Conditions
ConditionsYield
With bis(μ-chloro)-bis[1,3-di(2-pyridyl)-4,6-dimethylbenzene-N,C(2'),N-iridium chloride]; caesium carbonate In tert-Amyl alcohol for 12h; Reflux;85%
With [Ir(dpyx-N,C,N)Cl(i-Cl)]2; caesium carbonate In tert-Amyl alcohol at 130℃; for 2h; Reagent/catalyst;85%
With potassium phosphate tribasic trihydrate; C39H32Cl2N5PRu In tert-Amyl alcohol at 120℃; for 4h; Inert atmosphere; Schlenk technique;83%

1-benzyl-4-[((5,6-dimethoxy-2-ethoxycarbonylindan-1-on)-2-yl)methyl]piperidine

120014-06-4

donepezil

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 1h; Heating / reflux;80%
With potassium hydroxide In ethanol; water for 1h; Heating / reflux;80%

Donepezil Chemical Properties

Molecular Structure:

Molecular Formula: C24H29NO3
Molecular Weight: 379.492
IUPAC Name: 2-[(1-Benzylpiperidin-4-yl)methyl]-5,6-dimethoxy-2,3-dihydroinden-1-one
Synonyms of Donepezil (CAS NO.120014-06-4): Donepezil [INN:BAN] ; UNII-8SSC91326P ; 1H-Inden-1-one, 2,3-dihydro-5,6-dimethoxy-2-((1-(phenylmethyl)-4-piperidinyl)methyl)-
CAS NO: 120014-06-4
Classification Code: Central Nervous System Agents ; Cholinergic Agents ; Cholinesterase Inhibitors ; Enzyme Inhibitors ; Neurotransmitter Agents ; Nootropic Agents
Melting point: 207°C 
Index of Refraction: 1.578
Molar Refractivity: 110.39 cm3
Molar Volume: 332.4 cm3
Surface Tension: 45.2 dyne/cm
Density: 1.141 g/cm3
Flash Point: 273.1 °C
Enthalpy of Vaporization: 80.26 kJ/mol
Boiling Point: 527.9 °C at 760 mmHg
Vapour Pressure: 3.11E-11 mmHg at 25°C

Donepezil Uses

 Donepezil (CAS NO.120014-06-4) is used as an anti-dementia drug. Donepezil has been found to improve sleep apnea in Alzheimer's patients, it also can improve speech in children with autism.

Donepezil Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
women TDLo oral 1mg/kg (1mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

GASTROINTESTINAL: NAUSEA OR VOMITING		 Annals of Pharmacotherpy. Vol. 33, Pg. 812, 1999.

Donepezil Safety Profile

Safety Information of Donepezil (CAS NO.120014-06-4):
Hazard Codes: Xi
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
RIDADR: UN 2811

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