5,6-Dimethoxy-2-(piperidin-4-yl)methylene-indan-1-one supplier

Name
5,6-Dimethoxy-2-(piperidin-4-yl)methylene-indan-1-one
EINECS
CAS No. 120014-30-4
Article Data18
CAS DataBase
Density 1.116 g/cm³
Solubility
Melting Point 258-260°C (dec.)
Formula C₁₇H₂₃NO₃
Boiling Point 454.109 °C at 760 mmHg
Molecular Weight 289.375
Flash Point 228.437 °C
Transport Information
Appearance
Safety
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 5,6-Dimethoxy-2-(pyridine-4-Yl)Methylene-Indan-1-one base;5,6-Dimethoxy-2-(piperidin-4-yl)methyl-indan-1-one;5,6-Dimethoxy-2-(pyridin-4-Yl)Methyleneindan-1-one;5,6-Dimethoxy-2-(pyridin-4-yl)-Methyleneindan-1-one;4-[(5,6-Dimethoxy-1-indanone) -2-methyl] piperidine;4-[(5,6-Dimethoxy-1-indanon-2-yl) methyl] piperidine;
PSA 47.56000
LogP 2.77730

Synthetic route

: 4803-57-0
2-(pyridin-4-yl)methyl-5,6-dimethoxy-1-indanone

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
With hydrogen; platinum(IV) oxide In methanol; acetic acid at 20℃; under 2311.54 Torr; for 6h;	99%
With palladium on activated charcoal; hydrogen; acetic acid In methanol	74%
With 5% Pd(II)/C(eggshell); hydrogen; sodium acetate; acetic acid In methanol; dichloromethane at 70 - 75℃; under 4413.43 - 5149.01 Torr; for 10h;	70%

: 120014-06-4
donepezil

: 120014-30-4
debenzyldonepezil

Conditions

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;

: 861675-47-0
5,6-dimethoxy-2-(4-piperidinylmethyl)-indan-1-one acetate

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
In water pH=13;	95.3%

: (E)-tert-butyl 4-((5,6-dimethoxy-1-oxo-1H-inden-2(3H)-ylidene)methyl)piperidine-1-carboxylate

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Stage #1: (E)-tert-butyl 4-((5,6-dimethoxy-1-oxo-1H-inden-2(3H)-ylidene)methyl)piperidine-1-carboxylate With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; under 760.051 Torr; for 0.333333h; Stage #2: With hydrogenchloride In water; ethyl acetate at 20℃; for 3h;	91%

: 877606-65-0
(E)-5, 6-dimethoxy-2-(pyridin-4-ylmethylene)-2, 3-dihydro-1H-inden-1-one

A: 4803-57-0
2-(pyridin-4-yl)methyl-5,6-dimethoxy-1-indanone

B: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
With hydrogen; acetic acid; palladium on activated charcoal In methanol at 60 - 65℃; for 7h;	A n/a B 90%

: 5,6-dimethoxy-3-(pyridine-4-yl)spiro[indene-2,2'-oxiran]-1(3H)-one

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
With perchloric acid; 5% Pd(II)/C(eggshell); hydrogen In methanol; dichloromethane at 60 - 65℃; under 4781.22 Torr; for 10h;	90%

: 948550-60-5
tert-butyl 4-((2,3-dihydro-5,6-dimethoxy-1-oxo-1H-inden-2-yl)-methyl)piperidine-1-carboxylate

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Stage #1: tert-butyl 4-((2,3-dihydro-5,6-dimethoxy-1-oxo-1H-inden-2-yl)-methyl)piperidine-1-carboxylate With hydrogenchloride In ethyl acetate Stage #2: With sodium carbonate In water; ethyl acetate pH=~ 6;	84%
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 4h;	80%

: (2E)-5,6-dimethoxy-2-(pyridin-4-yl-methylene)indan-1-one-N-oxide

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol; dichloromethane at 75 - 80℃; under 7355.72 Torr; for 8h;	77%

: 5,6-dimethoxy-3-(pyridine-4-yl)spiro[indene-2,2'-oxiran]-1(3H)-one

A: 844694-83-3
4-((5,6-dimethoxy-2,3-dihydro-1H-inden-2-yl)methyl)piperidine

B: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
With perchloric acid; palladium 10% on activated carbon; hydrogen In methanol at 70 - 75℃; under 4413.43 - 5149.01 Torr; for 7h;	A 22% B 63%

: 6457-49-4
4-piperidinemethanol

: 2107-69-9
5,6-dimethoxy-1-indanone

: 120014-30-4
debenzyldonepezil

Conditions

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;	51%

: 872-85-5
pyridine-4-carbaldehyde

N6-protected N2-Fmoc-lysine on Wang resin: N6-protected N2-Fmoc-lysine on Wang resin

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Multi-step reaction with 2 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 View Scheme

: 2107-69-9
5,6-dimethoxy-1-indanone

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Multi-step reaction with 2 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 View Scheme
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / toluene / Reflux 2: dihydrogen peroxide / acetic acid / 45 - 50 °C 3: palladium on activated charcoal; hydrogen / methanol; dichloromethane / 8 h / 75 - 80 °C / 7355.72 Torr View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h 1.2: 2 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 0.33 h / 20 °C / 760.05 Torr 2.2: 3 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 24 h / Reflux 2: hydrogen / neat (no solvent) / 144 h / 50 °C / 760.05 Torr View Scheme
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene 2: acetic acid; palladium on activated charcoal; hydrogen / methanol View Scheme

: 120014-07-5
1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine

A: donepezil hydrochloride

B: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Stage #1: 1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine With hydrogen; 5% Pd on alumina In tetrahydrofuran at 3 - 6℃; under 3000.3 - 7500.75 Torr; for 3 - 5h; Stage #2: With hydrogenchloride In tetrahydrofuran; ethanol; water Product distribution / selectivity;
Stage #1: 1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine With hydrogen; 5% Pd on alumina In tetrahydrofuran at 14 - 20℃; under 3750.38 - 7500.75 Torr; for 0.833333h; Stage #2: With hydrogenchloride In tetrahydrofuran; water
Stage #1: 1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine With hydrogen; 5% Pd on alumina In toluene at 9 - 12℃; under 1500.15 - 6000.6 Torr; for 2.33333 - 5h; Stage #2: With hydrogenchloride In ethanol; water; toluene Product distribution / selectivity;
Stage #1: 1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine With hydrogen; 5%-palladium/activated carbon In tetrahydrofuran; toluene at 30 - 60℃; under 1551.49 - 1810.07 Torr; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene at 25 - 30℃; Product distribution / selectivity;

: 120014-07-5
1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine

A: 120014-06-4
donepezil

B: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran at 0 - 2℃; under 760.051 Torr; for 1.5h;
With hydrogen; palladium 10% on activated carbon In toluene at 0 - 1℃; under 6000.6 - 7500.75 Torr; for 5h;

: 5,6-dimethoxy-2-[1-(4-pyridinyl)methylidene]-1-indanone tosylate

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In water at 60 - 95℃; under 7500.75 Torr; for 8h;

: 942424-77-3
5,6-dimethoxy-2-(pyridine-4-ylmethylene)indan-1-one hydrochloride

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
With hydrogen; acetic acid; palladium 10% on activated carbon In methanol at 68 - 72℃; under 3800.26 Torr; for 7h;

: 872-85-5
pyridine-4-carbaldehyde

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / toluene / Reflux 2: dihydrogen peroxide / acetic acid / 45 - 50 °C 3: palladium on activated charcoal; hydrogen / methanol; dichloromethane / 8 h / 75 - 80 °C / 7355.72 Torr View Scheme
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 24 h / Reflux 2: hydrogen / neat (no solvent) / 144 h / 50 °C / 760.05 Torr View Scheme
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene 2: acetic acid; palladium on activated charcoal; hydrogen / methanol View Scheme

: 877606-65-0
(E)-5, 6-dimethoxy-2-(pyridin-4-ylmethylene)-2, 3-dihydro-1H-inden-1-one

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dihydrogen peroxide / acetic acid / 45 - 50 °C 2: palladium on activated charcoal; hydrogen / methanol; dichloromethane / 8 h / 75 - 80 °C / 7355.72 Torr View Scheme
With hydrogen In neat (no solvent) at 50℃; under 760.051 Torr; for 144h;

: 6457-49-4
4-piperidinemethanol

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: tetrahydrofuran; ethyl acetate / 6 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / Inert atmosphere; Reflux 3.1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane; water / 0.5 h / 20 °C / Inert atmosphere 3.2: 5 h / 50 °C / Inert atmosphere 4.1: diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) / chloroform / 24 h / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: tetrahydrofuran; ethyl acetate / 6 h / 20 °C
2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / Inert atmosphere; Reflux
3.1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane; water / 0.5 h / 20 °C / Inert atmosphere
3.2: 5 h / 50 °C / Inert atmosphere
4.1: diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) / chloroform / 24 h / 20 °C
5.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C
View Scheme

: 137076-22-3
tert butyl 4-formylpiperidine-1-carboxylate

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane; water / 0.5 h / 20 °C / Inert atmosphere 1.2: 5 h / 50 °C / Inert atmosphere 2.1: diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) / chloroform / 24 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h 1.2: 2 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 0.33 h / 20 °C / 760.05 Torr 2.2: 3 h / 20 °C View Scheme

: 1126-09-6
4-carbethoxypiperidine

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 2.1: tetrahydrofuran; ethyl acetate / 6 h / 20 °C 3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / Inert atmosphere; Reflux 4.1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane; water / 0.5 h / 20 °C / Inert atmosphere 4.2: 5 h / 50 °C / Inert atmosphere 5.1: diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) / chloroform / 24 h / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2.1: tetrahydrofuran; ethyl acetate / 6 h / 20 °C
3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / Inert atmosphere; Reflux
4.1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane; water / 0.5 h / 20 °C / Inert atmosphere
4.2: 5 h / 50 °C / Inert atmosphere
5.1: diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) / chloroform / 24 h / 20 °C
6.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C
View Scheme

: 123855-51-6
tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylate

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / Inert atmosphere; Reflux 2.1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane; water / 0.5 h / 20 °C / Inert atmosphere 2.2: 5 h / 50 °C / Inert atmosphere 3.1: diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) / chloroform / 24 h / 20 °C 4.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h 2.2: 2 h / 20 °C 3.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 0.33 h / 20 °C / 760.05 Torr 3.2: 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / Inert atmosphere; Reflux
2.1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane; water / 0.5 h / 20 °C / Inert atmosphere
2.2: 5 h / 50 °C / Inert atmosphere
3.1: diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) / chloroform / 24 h / 20 °C
4.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C
View Scheme

Multi-step reaction with 3 steps
1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 20 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h
2.2: 2 h / 20 °C
3.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 0.33 h / 20 °C / 760.05 Torr
3.2: 3 h / 20 °C
View Scheme

: 1020717-67-2
tert-butyl 4-((5,6-dimethoxy-1-oxo-1H-inden-2(3H)-ylidene)methyl)piperidine-1-carboxylate

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) / chloroform / 24 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C View Scheme

: 2107-70-2
3,4-methoxycinnamic acid

: 120014-30-4
debenzyldonepezil

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: phosphorus pentoxide; toluene-4-sulfonic acid / 0.08 h / 120 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h 2.2: 2 h / 20 °C 3.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 0.33 h / 20 °C / 760.05 Torr 3.2: 3 h / 20 °C View Scheme

: 24964-64-5
3-Cyanobenzaldehyde

: 120014-30-4
debenzyldonepezil

: 1-(3-cyanobenzyl)-4-[(5,6-dimethoxy-1-indanon)-2-yl]methylpiperidine

Conditions

Conditions	Yield
Stage #1: 3-Cyanobenzaldehyde; debenzyldonepezil In 1,2-dichloro-ethane Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 3h;	100%
With sodium tris(acetoxy)borohydride; acetic acid In ethyl acetate; 1,2-dichloro-ethane

: 120014-30-4
debenzyldonepezil

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

Conditions

Conditions	Yield
With hydrogenchloride In water; toluene at 10℃; Temperature; Reflux;	95.35%

: 17329-87-2
2-chloro-N-(4-nitro-phenyl)-acetamide

: 120014-30-4
debenzyldonepezil

: 2-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)-N-(p-nitrophenyl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 12h;	93%

: 100-39-0
benzyl bromide

: 120014-30-4
debenzyldonepezil

: 120014-06-4
donepezil

Conditions

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

: 3958-60-9
2-nitrophenylmethyl bromide

: 120014-30-4
debenzyldonepezil

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

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 8h; Reflux;	92%

: 100-11-8
1-bromomethyl-4-nitro-benzene

: 120014-30-4
debenzyldonepezil

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

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 8h; Reflux;	92%

: 3427-30-3
2-chloro-N-(6-methoxy-1,3-benzothiazol-2-yl)acetamide

: 120014-30-4
debenzyldonepezil

: N-(6-methoxybenzo[d]thiazol-2-yl)-2-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 12h;	92%

: 587-65-5
N-chloroacetyl-aniline

: 120014-30-4
debenzyldonepezil

: 2-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)-N-phenylacetamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 12h;	92%

: 351-04-2
2-chloro-N-(4-fluorophenyl)acetamide

: 120014-30-4
debenzyldonepezil

: 2-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)-N-(p-fluorophenyl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 12h;	91%

: 3289-75-6
2-chloro-N-(4-chlorophenyl)acetamide

: 120014-30-4
debenzyldonepezil

: 2-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)-N-(p-chlorophenyl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 12h;	90%

: 120014-30-4
debenzyldonepezil

: 3028-02-2
N-benzothiazol-2-yl-2-chloroacetamide

: N-(benzo[d]thiazol-2-yl)-2-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 12h;	89%

: 120014-30-4
debenzyldonepezil

: 2-chloro-N-(6-nitro-1,3-benzothiazol-2-yl)acetamide

: N-(6-nitrobenzo[d]thiazol-2-yl)-2-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 12h;	89%

: 120014-30-4
debenzyldonepezil

: 22303-36-2
N-(4-methoxyphenyl)-2-chloroacetamide

: 2-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)-N-(p-methoxyphenyl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 12h;	89%

: 100202-78-6
2-(bromomethyl)-6-fluoropyridine

: 120014-30-4
debenzyldonepezil

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

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 8h; Reflux;	88%

: 10136-57-9
5-(chloromethyl)quinolin-8-ol

: 120014-30-4
debenzyldonepezil

: 2-((1-((8-hydroxyquinolin-5-yl)methyl)piperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 8h; Reflux;	88%

: 263239-23-2
2-chloro-N-(6-fluorobenzo[d]thiazol-2-yl)acetamide

: 120014-30-4
debenzyldonepezil

: N-(6-fluorobenzo[d]thiazol-2-yl)-2-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 12h;	88%

: 625-55-8
isopropyl formate

: 120014-30-4
debenzyldonepezil

: 4-(2,3-dihydro-5,6-dimethoxy-1-indanone-2-ylmethyl)piperidine-1-carbaldehyde

Conditions

Conditions	Yield
Stage #1: debenzyldonepezil With potassium carbonate In methanol; water at 20℃; for 2h; Stage #2: isopropyl formate at 50℃; for 2h;	88%

: 120014-30-4
debenzyldonepezil

: 3174-15-0
2-chloro-N-(6-methylbenzothiazol-2-yl)acetamide

: N-(6-methylbenzo[d]thiazol-2-yl)-2-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 12h;	87%

: 62593-78-6
2-chloro-N1-(3,4-dimethoxyphenyl)-acetamide

: 120014-30-4
debenzyldonepezil

: 2-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)-N-(3,4-dimethoxyphenyl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 12h;	87%

: 107-13-1
acrylonitrile

: 120014-30-4
debenzyldonepezil

: 3-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)propanenitrile

Conditions

Conditions	Yield
With sodium In methanol at 55℃; for 12h; Inert atmosphere;	87%

: 459-46-1
4-Fluorobenzyl bromide

: 120014-30-4
debenzyldonepezil

: 351532-09-7
2-((1-(4-fluorobenzyl)piperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 8h; Reflux;	86%

: 16634-82-5
N-(p-tolyl)-2-chloroacetamide

: 120014-30-4
debenzyldonepezil

: 2-(4-((5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)piperidin-1-yl)-N-(p-tolyl)acetamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 12h;	86%

: 126300-99-0, 149356-90-1
(S)-2-[1-(tert-butoxycarbonylamino)-2-methylpropyl]thiazole-4-carboxylic acid

: 120014-30-4
debenzyldonepezil

: 1609138-31-9
C30H41N3O6S

Conditions

Conditions	Yield
Stage #1: (S)-2-[1-(tert-butoxycarbonylamino)-2-methylpropyl]thiazole-4-carboxylic acid With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 0℃; for 0.166667h; Stage #2: debenzyldonepezil In N,N-dimethyl acetamide at 20℃; for 18h;	85%

: 170289-36-8
2-bromomethyl-3,5-dimethylpyridine

: 120014-30-4
debenzyldonepezil

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

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 8h; Reflux;	85%

5,6-Dimethoxy-2-(piperidin-4-yl)methylene-indan-1-one Specification

The 5,6-Dimethoxy-2-(piperidin-4-yl)methylene-indan-1-one with CAS registry number of 120014-30-4 is also known as 4-[(5,6-Dimethoxy-1-indanon-2-yl) methyl] piperidine. The IUPAC name is 5,6-Dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydroinden-1-one. It belongs to product categories of (Intermediate of donepezil); Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals; Print Catalog. In addition, the formula is C₁₇H₂₃NO₃ and the molecular weight is 289.37. This chemical can be used as intermediates of organic synthesis and pharmaceutical synthesis. It's also can be used for synthesis of donepezil.

Physical properties about 5,6-Dimethoxy-2-(piperidin-4-yl)methylene-indan-1-one are: (1)ACD/LogP: 1.59; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0; (4)ACD/LogD (pH 7.4): 0; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.538; (13)Molar Refractivity: 81.013 cm³; (14)Molar Volume: 259.136 cm³; (15)Surface Tension: 39.601 dyne/cm; (16)Density: 1.117 g/cm³; (17)Flash Point: 228.437 °C; (18)Enthalpy of Vaporization: 71.363 kJ/mol; (19)Boiling Point: 454.109 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: COC1=C(C=C2C(=C1)CC(C2=O)CC3CCNCC3)OC
2. InChI: InChI=1S/C17H23NO3/c1-20-15-9-12-8-13(7-11-3-5-18-6-4-11)17(19)14(12)10-16(15)21-2/h9-11,13,18H,3-8H2,1-2H3
3. InChIKey: PGBZORAISITZTF-UHFFFAOYSA-N

Product Name

5,6-Dimethoxy-2-(piperidin-4-yl)methylene-indan-1-one

Synthetic route

5,6-Dimethoxy-2-(piperidin-4-yl)methylene-indan-1-one Specification

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