donepezil
Conditions | Yield |
---|---|
In methanol | 99% |
donepezil
Conditions | Yield |
---|---|
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; |
benzyl bromide
donepezil
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide Product distribution / selectivity; | 96% |
Conditions | Yield |
---|---|
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 |
2-(3,4-dimethoxybenzyl)-3-(N-benzyl-4-piperidine)propionic acid
donepezil
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; trifluoroacetic anhydride In dichloromethane at 24 - 28℃; Inert atmosphere; chemoselective reaction; | 90% |
donepezil
Conditions | Yield |
---|---|
With sodium dithionite; tetrabutylammomium bromide; sodium hydrogencarbonate In water; ethyl acetate | 88% |
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. |
Conditions | Yield |
---|---|
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 |
1-benzyl-4-[(5,6-dimethoxy-1-indanol)-2-yl]methylpiperidine
donepezil
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; tetrabutylammomium bromide In decane; benzene at 40℃; for 24h; Sealed tube; chemoselective reaction; | 85% |
Conditions | Yield |
---|---|
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% |
donepezil
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water for 1h; Heating / reflux; | 80% |
With potassium hydroxide In ethanol; water for 1h; Heating / reflux; | 80% |
donepezil
Conditions | Yield |
---|---|
With acetic acid; L-proline at 120℃; for 24h; Green chemistry; | 77% |
donepezil
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water | 76.34% |
benzaldehyde
donepezil
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-5,6-dimethoxy-2-((piperidin-4-yl)methyl)inden-1-one p-toluenesulfonic acid salt With hydrogen; sodium acetate; palladium 10% on activated carbon In methanol under 760.051 Torr; for 10h; Stage #2: benzaldehyde In methanol for 8h; Product distribution / selectivity; | 62% |
5-[(1-benzyl-4-piperidyl)methyl]-5-(3,4-dimethoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
donepezil
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In nitromethane at 100℃; for 0.5h; Friedel-Crafts acylation; | 61% |
Conditions | Yield |
---|---|
With trifuran-2-yl-phosphane; C42H32F3N2O2PPd; lithium hydroxide In neat (no solvent) at 100℃; for 48h; Schlenk technique; Sealed tube; Inert atmosphere; Green chemistry; chemoselective reaction; | 56% |
donepezil
Conditions | Yield |
---|---|
With platinum(IV) oxide; hydrogen In methanol at 23℃; under 760.051 Torr; for 24h; Inert atmosphere; | 50% |
2-((1-benzoylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
donepezil
Conditions | Yield |
---|---|
With trifluoromethylsulfonic anhydride; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In dichloromethane at 20℃; for 2h; | 49% |
1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine
donepezil
Conditions | Yield |
---|---|
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 16h; | 37% |
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran at 20℃; under 760.051 Torr; for 6h; | |
With hydrogen; nickel In tetrahydrofuran at 8 - 38℃; under 750.075 - 9000.9 Torr; for 0.666667 - 6h; Product distribution / selectivity; |
donepezil
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In tetrahydrofuran under 760 Torr; for 6h; Ambient temperature; | |
Stage #1: 1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine hydrochloride In methanol; acetic acid at 25 - 45℃; Stage #2: With hydrogen; 5%-palladium/activated carbon In methanol; acetic acid under 1103.36 - 1471.14 Torr; | |
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 6h; | |
Stage #1: 1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine hydrochloride With hydrogen; acetic acid; 5% Pd(II)/C(eggshell) In methanol at 28 - 33℃; under 1103.36 - 1471.14 Torr; Stage #2: With sodium carbonate In dichloromethane; water for 7 - 8h; Stage #3: With hydrogenchloride In isopropyl alcohol at 25 - 30℃; pH=2; |
Conditions | Yield |
---|---|
With sodium carbonate In methanol; isopropyl alcohol at 60 - 65℃; for 11h; |
5,6-dimethoxy-1-indanone
donepezil
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / methanol; H2O / Heating 1.2: 77 percent / methanol; H2O / 2.5 h / 75 °C 2.1: 31 g / H2 / palladium carbon / methanol / 2 h / 20 °C / 760.05 Torr View Scheme | |
Multi-step reaction with 3 steps 1: 95.6 percent / p-toluenesulfonic acid / toluene / 6 h / Heating 2: 90 percent / hydrogen; acetic acid / palladium on activated charcoal / methanol / 7 h / 60 - 65 °C 3: sodium carbonate / methanol; propan-2-ol / 11 h / 60 - 65 °C View Scheme | |
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium hydroxide / water; dichloromethane / 1.5 h / 38 °C 2: tetrabutylammomium bromide; sodium hydrogencarbonate; sodium dithionite / water; ethyl acetate View Scheme | |
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium hydroxide / dichloromethane; water / 1.5 h / 38 °C 2: tetrabutylammomium bromide; sodium hydrogencarbonate; sodium dithionite; water / ethyl acetate / 0.5 h / 65 °C View Scheme | |
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / toluene / 24 h / Reflux 2: hydrogen / neat (no solvent) / 144 h / 50 °C / 760.05 Torr 3: sodium carbonate / isopropyl alcohol / 12 h / 50 °C View Scheme |
1-benzyl-4-formylpiperidine
donepezil
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / methanol; H2O / Heating 1.2: 77 percent / methanol; H2O / 2.5 h / 75 °C 2.1: 31 g / H2 / palladium carbon / methanol / 2 h / 20 °C / 760.05 Torr View Scheme | |
Multi-step reaction with 3 steps 1.1: piperidinium acetate / ethanol / 0.5 h 1.2: 47 percent / NaBH3CN / ethanol / 0 - 20 °C 2.1: 44 percent / K2CO3 / dimethylformamide 3.1: 61 percent / TfOH / nitromethane / 0.5 h / 100 °C View Scheme | |
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium hydroxide / water; dichloromethane / 1.5 h / 38 °C 2: tetrabutylammomium bromide; sodium hydrogencarbonate; sodium dithionite / water; ethyl acetate View Scheme |
pyridine-4-carbaldehyde
donepezil
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 95.6 percent / p-toluenesulfonic acid / toluene / 6 h / Heating 2: 90 percent / hydrogen; acetic acid / palladium on activated charcoal / methanol / 7 h / 60 - 65 °C 3: sodium carbonate / methanol; propan-2-ol / 11 h / 60 - 65 °C View Scheme |
(E)-5, 6-dimethoxy-2-(pyridin-4-ylmethylene)-2, 3-dihydro-1H-inden-1-one
donepezil
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / hydrogen; acetic acid / palladium on activated charcoal / methanol / 7 h / 60 - 65 °C 2: sodium carbonate / methanol; propan-2-ol / 11 h / 60 - 65 °C View Scheme | |
Multi-step reaction with 2 steps 1: acetonitrile / 24 h / Reflux 2: platinum(IV) oxide; hydrogen / methanol / 24 h / 23 °C / 760.05 Torr / Inert atmosphere View Scheme |
5-(1-benzyl-piperidin-4-ylmethyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione
donepezil
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 44 percent / K2CO3 / dimethylformamide 2: 61 percent / TfOH / nitromethane / 0.5 h / 100 °C View Scheme |
benzyl bromide
donepezil
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; potassium carbonate In dichloromethane; water at 20 - 25℃; for 1h; | |
Stage #1: benzyl bromide; 5,6-dimethoxy-2-(piperidine-4-ylmethyl)-2,3-dihydro-1H-inden-1-one hydrochloride With monopotassium carbonate; tetrabutylammomium bromide In methylene chlorid; water at 20 - 25℃; for 1h; Stage #2: With hydrogenchloride In dichloromethane; water at 20 - 25℃; for 0.25h; Stage #3: With ammonia In water; ethyl acetate pH=9.5; |
donepezil
Conditions | Yield |
---|---|
With sodium hydroxide In water; toluene at 20 - 40℃; for 2h; |
Conditions | Yield |
---|---|
With potassium carbonate; tetra-(n-butyl)ammonium iodide In acetone at 60℃; | |
With potassium carbonate; polyethylene glycol In water; ethyl acetate at 45℃; | |
With potassium carbonate In water; ethyl acetate at 50 - 55℃; for 14h; Inert atmosphere; | |
With sodium hydrogencarbonate In ethanol at 65℃; for 0.5h; Temperature; |
benzaldehyde
donepezil
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydrogen; platinum on activated charcoal / toluene / 80 °C / Flow reactor 2: diisobutylaluminium hydride / toluene; hexane / 2.5 h / -78 °C / Flow reactor 3: water / isopropyl alcohol; tetrahydrofuran / 3 h / 55 °C / Flow reactor 4: hydrogen / isopropyl alcohol; water; tetrahydrofuran / 20 h / 25 °C / 760.05 Torr / Flow reactor View Scheme |
donepezil
Conditions | Yield |
---|---|
With [(2)H6]acetone; tris(pentafluorophenyl)borate In toluene at 150℃; for 3h; Inert atmosphere; | 98% |
donepezil
debenzyldonepezil
Conditions | Yield |
---|---|
With ammonium formate; palladium 10% on activated carbon In methanol at 20℃; for 3h; Heating / reflux; | 97% |
With hydrogen In methanol at 20℃; under 760.051 Torr; for 72h; |
donepezil
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol | 96.2% |
With hydrogenchloride In ethanol | 96.5% |
With hydrogenchloride In ethanol | 96.4% |
donepezil
donepezil-d1
Conditions | Yield |
---|---|
With tris(pentafluorophenyl)borate; water-d2 In tetrahydrofuran at 100℃; for 12h; Solvent; Inert atmosphere; regioselective reaction; | 96% |
With sodium methylate at 20℃; Reagent/catalyst; | 50% |
(2E)-but-2-enedioic acid
donepezil
Conditions | Yield |
---|---|
In ethanol at 20 - 60℃; for 2h; | 95.4% |
In ethanol; ethyl acetate at 20℃; Product distribution / selectivity; | |
In methanol at 25 - 30℃; for 5h; | 5.1 g |
In ethanol; water at 20 - 60℃; Sealed tube; |
chloroformic acid ethyl ester
donepezil
4-[(5,6-dimethoxy-1-indanon)-2-yl]methyl-1-ethoxycarbonylpiperidine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In benzene | 94% |
donepezil
Donepezil sulphate
Conditions | Yield |
---|---|
With sulfuric acid In isopropyl alcohol at 0℃; for 2h; | 92.4% |
With sulfuric acid In ethanol; ethyl acetate at 20℃; Product distribution / selectivity; |
maleic acid
donepezil
Conditions | Yield |
---|---|
In isopropyl alcohol at 20 - 60℃; for 1h; | 91.2% |
In water; toluene at 25 - 30℃; | 90% |
In ethanol; ethyl acetate at 20℃; Product distribution / selectivity; | |
In methanol; water at 20 - 100℃; Sealed tube; |
donepezil
Conditions | Yield |
---|---|
With hydrogen bromide In isopropyl alcohol | 89.9% |
With hydrogen bromide In ethanol; water at 10 - 35℃; for 12.33h; | 58.9% |
With hydrogen bromide In methanol; water Purification / work up; | |
With hydrogen bromide In methanol; water at 0 - 5℃; for 2 - 3h; |
Conditions | Yield |
---|---|
In isopropyl alcohol at 20℃; Heating / reflux; | 89.2% |
In ethanol; ethyl acetate at 20℃; Product distribution / selectivity; | |
In ethanol; ethyl acetate at 20℃; Product distribution / selectivity; | |
In isopropyl alcohol for 168h; |
Conditions | Yield |
---|---|
In isopropyl alcohol at 20℃; Heating / reflux; | 87.5% |
In ethanol; ethyl acetate Product distribution / selectivity; | |
In ethanol; ethyl acetate Product distribution / selectivity; | |
In isopropyl alcohol for 168h; | |
In ethanol; water at 20 - 80℃; Sealed tube; |
toluene-4-sulfonic acid
donepezil
Conditions | Yield |
---|---|
In isopropyl alcohol at 20℃; Heating / reflux; | 84.2% |
In ethanol; ethyl acetate at 20℃; Product distribution / selectivity; | |
In ethanol; ethyl acetate at 20℃; Product distribution / selectivity; | |
In ethyl acetate; acetone at 25 - 30℃; for 12h; | 6.5 g |
In isopropyl alcohol for 168h; |
Conditions | Yield |
---|---|
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; zinc(II) chloride; lithium diisopropyl amide at -10℃; for 12h; | 83% |
Conditions | Yield |
---|---|
Stage #1: n-heptanoic anhydride; donepezil With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 10℃; Inert atmosphere; Stage #2: In tetrahydrofuran at -78 - 30℃; | 81.7% |
donepezil
Conditions | Yield |
---|---|
With P2O5; MeSO3H In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane | 80% |
Ethyl bromodifluoroacetate
donepezil
Conditions | Yield |
---|---|
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; zinc(II) chloride; lithium diisopropyl amide at -10℃; for 12h; | 80% |
palmitic anhydride
donepezil
Conditions | Yield |
---|---|
Stage #1: palmitic anhydride; donepezil With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 10℃; Inert atmosphere; Stage #2: In tetrahydrofuran at -78 - 30℃; | 79.5% |
donepezil
Conditions | Yield |
---|---|
With hydrogen bromide; dimethyl sulfoxide In water; ethyl acetate at 60℃; | 78% |
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 (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.
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. |
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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