Product Name

  • Name

    2-[(1-Benzyl-4-piperidyl)methyl]-5,6-dimethoxy-2,3-dihydroinden-1-one

  • EINECS 601-651-9
  • CAS No. 120014-06-4
  • Article Data68
  • CAS DataBase
  • Density 1.141 g/cm3
  • 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
  • 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;
  • PSA 38.77000
  • LogP 4.29900

Synthetic route

ethyl acetate thrice

ethyl acetate thrice

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

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

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
In methanol99%
donepezil hydrochloride

donepezil hydrochloride

donepezil
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

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

benzyl bromide
100-39-0

benzyl bromide

donepezil
120014-06-4

donepezil

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

benzyl bromide

debenzyldonepezil
120014-30-4

debenzyldonepezil

donepezil
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
2-(3,4-dimethoxybenzyl)-3-(N-benzyl-4-piperidine)propionic acid
259170-03-1

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

donepezil
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

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

donepezil
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.
5,6-dimethoxy-1-indanone
2107-69-9

5,6-dimethoxy-1-indanone

1-benzyl-4-formylpiperidine
22065-85-6

1-benzyl-4-formylpiperidine

donepezil
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
1-benzyl-4-[(5,6-dimethoxy-1-indanol)-2-yl]methylpiperidine
120012-04-6

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

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
With tert.-butylhydroperoxide; tetrabutylammomium bromide In decane; benzene at 40℃; for 24h; Sealed tube; chemoselective reaction;85%
5,6-dimethoxy-1-indanone
2107-69-9

5,6-dimethoxy-1-indanone

1-benzyl-4-piperidinemethanol
67686-01-5

1-benzyl-4-piperidinemethanol

donepezil
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

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

donepezil
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%
C24H29NO3

C24H29NO3

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
With acetic acid; L-proline at 120℃; for 24h; Green chemistry;77%
2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-1-oxo-2,3-dihydro-1H-indene-2-carbonitrile

2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-1-oxo-2,3-dihydro-1H-indene-2-carbonitrile

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
With hydrogenchloride In methanol; water76.34%
2,3-dihydro-5,6-dimethoxy-2-((piperidin-4-yl)methyl)inden-1-one p-toluenesulfonic acid salt

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

benzaldehyde
100-52-7

benzaldehyde

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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
848610-96-8

5-[(1-benzyl-4-piperidyl)methyl]-5-(3,4-dimethoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In nitromethane at 100℃; for 0.5h; Friedel-Crafts acylation;61%
debenzyldonepezil
120014-30-4

debenzyldonepezil

benzyl alcohol
100-51-6

benzyl alcohol

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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%
(E)-1-benzyl-4-((5,6-dimethoxy-1-oxo-1,3-dihydro-2H-inden-2-ylidene)methyl)pyridin-1-ium bromide

(E)-1-benzyl-4-((5,6-dimethoxy-1-oxo-1,3-dihydro-2H-inden-2-ylidene)methyl)pyridin-1-ium bromide

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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
120013-38-9

2-((1-benzoylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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
120014-07-5

1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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;
1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine hydrochloride

1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine hydrochloride

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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;
benzyl bromide
100-39-0

benzyl bromide

debenzyldonepezil
120014-30-4

debenzyldonepezil

A

1,1-dibenzyl-4-(5,6-dimethoxy-1-oxo-indan-2-ylmethyl)-piperidinium; bromide

1,1-dibenzyl-4-(5,6-dimethoxy-1-oxo-indan-2-ylmethyl)-piperidinium; bromide

B

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
With sodium carbonate In methanol; isopropyl alcohol at 60 - 65℃; for 11h;
5,6-dimethoxy-1-indanone
2107-69-9

5,6-dimethoxy-1-indanone

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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
22065-85-6

1-benzyl-4-formylpiperidine

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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
872-85-5

pyridine-4-carbaldehyde

N6-protected N2-Fmoc-lysine on Wang resin

N6-protected N2-Fmoc-lysine on Wang resin

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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
877606-65-0

(E)-5, 6-dimethoxy-2-(pyridin-4-ylmethylene)-2, 3-dihydro-1H-inden-1-one

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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
865718-00-9

5-(1-benzyl-piperidin-4-ylmethyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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
100-39-0

benzyl bromide

5,6-dimethoxy-2-(piperidine-4-ylmethyl)-2,3-dihydro-1H-inden-1-one hydrochloride

5,6-dimethoxy-2-(piperidine-4-ylmethyl)-2,3-dihydro-1H-inden-1-one hydrochloride

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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;
1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidenyl]methylpiperidine maleate

1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidenyl]methylpiperidine maleate

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
With sodium hydroxide In water; toluene at 20 - 40℃; for 2h;
benzyl chloride
100-44-7

benzyl chloride

debenzyldonepezil
120014-30-4

debenzyldonepezil

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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
100-52-7

benzaldehyde

donepezil
120014-06-4

donepezil

Conditions
ConditionsYield
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
120014-06-4

donepezil

C24H24(2)H5NO3

C24H24(2)H5NO3

Conditions
ConditionsYield
With [(2)H6]acetone; tris(pentafluorophenyl)borate In toluene at 150℃; for 3h; Inert atmosphere;98%
donepezil
120014-06-4

donepezil

debenzyldonepezil
120014-30-4

debenzyldonepezil

Conditions
ConditionsYield
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
120014-06-4

donepezil

donepezil hydrochloride

donepezil hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol96.2%
With hydrogenchloride In ethanol96.5%
With hydrogenchloride In ethanol96.4%
donepezil
120014-06-4

donepezil

donepezil-d1
1228545-52-5

donepezil-d1

Conditions
ConditionsYield
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
110-17-8

(2E)-but-2-enedioic acid

donepezil
120014-06-4

donepezil

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

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

Conditions
ConditionsYield
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
541-41-3

chloroformic acid ethyl ester

donepezil
120014-06-4

donepezil

4-[(5,6-dimethoxy-1-indanon)-2-yl]methyl-1-ethoxycarbonylpiperidine
120013-42-5

4-[(5,6-dimethoxy-1-indanon)-2-yl]methyl-1-ethoxycarbonylpiperidine

Conditions
ConditionsYield
With sodium hydrogencarbonate In benzene94%
donepezil
120014-06-4

donepezil

Donepezil sulphate
881405-91-0

Donepezil sulphate

Conditions
ConditionsYield
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
110-16-7

maleic acid

donepezil
120014-06-4

donepezil

1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidenyl]methylpiperidine maleate

1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidenyl]methylpiperidine maleate

Conditions
ConditionsYield
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
120014-06-4

donepezil

1-benzyl-4-(5,6-dimethoxy-1-indanon-2-yl)methylpiperidine hydrobromide

1-benzyl-4-(5,6-dimethoxy-1-indanon-2-yl)methylpiperidine hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In isopropyl alcohol89.9%
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;
methanesulfonic acid
75-75-2

methanesulfonic acid

donepezil
120014-06-4

donepezil

donepezil methanesulfonate

donepezil methanesulfonate

Conditions
ConditionsYield
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;
donepezil
120014-06-4

donepezil

benzenesulfonic acid
98-11-3

benzenesulfonic acid

donepezil benzenenesulfonate

donepezil benzenenesulfonate

Conditions
ConditionsYield
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
104-15-4

toluene-4-sulfonic acid

donepezil
120014-06-4

donepezil

1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-yl]methylpiperidine p-toluenesulphonate

1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-yl]methylpiperidine p-toluenesulphonate

Conditions
ConditionsYield
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;
donepezil
120014-06-4

donepezil

2-(1-bromodifluoromethyl)benzo-1,3-oxazole
186828-50-2

2-(1-bromodifluoromethyl)benzo-1,3-oxazole

C32H32F2N2O4

C32H32F2N2O4

Conditions
ConditionsYield
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%
n-heptanoic anhydride
626-27-7

n-heptanoic anhydride

donepezil
120014-06-4

donepezil

donepezil enanthate

donepezil enanthate

Conditions
ConditionsYield
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%
i-Pr2O

i-Pr2O

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

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

donepezil
120014-06-4

donepezil

donepezil hydrochloride

donepezil hydrochloride

Conditions
ConditionsYield
With P2O5; MeSO3H In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane80%
Ethyl bromodifluoroacetate
667-27-6

Ethyl bromodifluoroacetate

donepezil
120014-06-4

donepezil

ethyl 2-(2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)-2,2-difluoroacetate

ethyl 2-(2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)-2,2-difluoroacetate

Conditions
ConditionsYield
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
623-65-4

palmitic anhydride

donepezil
120014-06-4

donepezil

2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-1H-inden-3-ylpalmitate

2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-1H-inden-3-ylpalmitate

Conditions
ConditionsYield
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
120014-06-4

donepezil

2-((1-benzylpiperidin-4-yl)methyl)-2-bromo-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

2-((1-benzylpiperidin-4-yl)methyl)-2-bromo-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Conditions
ConditionsYield
With hydrogen bromide; dimethyl sulfoxide In water; ethyl acetate at 60℃;78%

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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