Name: Itopride hydrochloride
SKU: 122892-31-3

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Basic Information

Molecular Structure:
CAS No.:	122892-31-3
Name:	Itopride hydrochloride
Article Data:	10

Formula:	C₂₀H₂₆N₂O₄^.HCl
Molecular Weight:	394.898
Synonyms:	Benzamide,N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4-dimethoxy-, monohydrochloride(9CI);Ganaton;HSR 803;
EINECS:	602-905-1
Melting Point:	194-195 °C
Boiling Point:	510.1 °C at 760 mmHg
Flash Point:	262.3 °C
Appearance:	white or pale brownish crystal
Hazard Symbols:	N
Risk Codes:	50
Safety:	61
PSA:	60.03000
LogP:	3.76710

Synthetic route

: 122898-67-3
itopride

: 122892-31-3
N-<4-<2-(dimethylamino)ethoxy>benzyl>-3,4-dimethoxybenzamide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water; iso-butanol at 50 - 55℃; for 0.5h; pH=2.0;	93.7%
With hydrogenchloride In ethanol at 0℃;	93%
With hydrogenchloride In ethanol	90%
With hydrogenchloride In isopropyl alcohol at 25 - 30℃; for 0.5h; pH=1 - 2;	79%
With hydrogenchloride In isopropyl alcohol at 25 - 30℃; for 0.5h; pH=1 - 2;	79%

: 2024-83-1
veratronitrile

: 131028-54-1
(4-(2-(dimethylamino)ethoxy)phenyl)methanol

: 122898-67-3
itopride

: 122892-31-3
N-<4-<2-(dimethylamino)ethoxy>benzyl>-3,4-dimethoxybenzamide hydrochloride

Conditions

Conditions	Yield
Stage #1: veratronitrile; (4-(2-(dimethylamino)ethoxy)phenyl)methanol With trifluorormethanesulfonic acid In toluene at 80℃; for 8h; Stage #2: itopride With hydrogenchloride In ethanol at 0℃; Reagent/catalyst;	93%

...Expand

: 943518-63-6
N-(4-hydroxybenzyl)-3,4-dimethoxybenzamide

: 107-99-3
2-(dimethylamino)ethyl chloride

: 122892-31-3
N-<4-<2-(dimethylamino)ethoxy>benzyl>-3,4-dimethoxybenzamide hydrochloride

Conditions

Conditions	Yield
With potassium iodide In N,N-dimethyl-formamide at 130 - 135℃; Temperature;	87%

: 108-01-0
2-(N,N-dimethylamino)ethanol

: 4-((3,4-dimethoxybenzamido)methyl)phenyl methanesulfonate

: 122892-31-3
N-<4-<2-(dimethylamino)ethoxy>benzyl>-3,4-dimethoxybenzamide hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-(N,N-dimethylamino)ethanol With sodium hydroxide In toluene for 0.5h; Reflux; Stage #2: 4-((3,4-dimethoxybenzamido)methyl)phenyl methanesulfonate In toluene for 1.5h; Reflux; Stage #3: With hydrogenchloride In dichloromethane; water for 0.5h;	80%

: 767-00-0
4-cyanophenol

: 122892-31-3
N-<4-<2-(dimethylamino)ethoxy>benzyl>-3,4-dimethoxybenzamide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 0.5 h 1.2: 1 h 2.1: nickel dichloride; sodium tetrahydroborate / ethanol / 0.5 h / 20 - 25 °C 3.1: triethylamine / methanol / 2 h 4.1: sodium hydroxide / toluene / 0.5 h / Reflux 4.2: 1.5 h / Reflux 4.3: 0.5 h View Scheme
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 0.5 h 1.2: 1 h 2.1: nickel dichloride; sodium tetrahydroborate / ethanol / 0.5 h / 20 - 25 °C 3.1: 1-hydroxy-pyrrolidine-2,5-dione / dichloromethane / 0.17 h / -10 - 0 °C 3.2: 2 h / Reflux 3.3: 2 h / Reflux 4.1: sodium hydroxide / toluene / 0.5 h / Reflux 4.2: 1.5 h / Reflux 4.3: 0.5 h View Scheme

: 138373-10-1
4-cyanophenyl mesylate

: 122892-31-3
N-<4-<2-(dimethylamino)ethoxy>benzyl>-3,4-dimethoxybenzamide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: nickel dichloride; sodium tetrahydroborate / ethanol / 0.5 h / 20 - 25 °C 2.1: triethylamine / methanol / 2 h 3.1: sodium hydroxide / toluene / 0.5 h / Reflux 3.2: 1.5 h / Reflux 3.3: 0.5 h View Scheme
Multi-step reaction with 3 steps 1.1: nickel dichloride; sodium tetrahydroborate / ethanol / 0.5 h / 20 - 25 °C 2.1: 1-hydroxy-pyrrolidine-2,5-dione / dichloromethane / 0.17 h / -10 - 0 °C 2.2: 2 h / Reflux 2.3: 2 h / Reflux 3.1: sodium hydroxide / toluene / 0.5 h / Reflux 3.2: 1.5 h / Reflux 3.3: 0.5 h View Scheme

: 1052148-15-8
(4-methanesulfonyloxyphenylmethane)amine

: 122892-31-3
N-<4-<2-(dimethylamino)ethoxy>benzyl>-3,4-dimethoxybenzamide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / methanol / 2 h 2.1: sodium hydroxide / toluene / 0.5 h / Reflux 2.2: 1.5 h / Reflux 2.3: 0.5 h View Scheme

: 108-95-2
phenol

: 122892-31-3
N-<4-<2-(dimethylamino)ethoxy>benzyl>-3,4-dimethoxybenzamide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium hydroxide / ethanol; water / 4 h / 55 - 60 °C 2: hydrogenchloride / water / 2 h / -10 °C 3: ammonium hydroxide / methanol / 6 h / 80 °C / Autoclave 4: N-ethyl-N,N-diisopropylamine / toluene / 2 h / 70 °C / Cooling with ice 5: hydrogenchloride / ethanol View Scheme

: 13468-02-5
dimethyl(2-phenoxyethyl)amine

: 122892-31-3
N-<4-<2-(dimethylamino)ethoxy>benzyl>-3,4-dimethoxybenzamide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 2 h / -10 °C 2: ammonium hydroxide / methanol / 6 h / 80 °C / Autoclave 3: N-ethyl-N,N-diisopropylamine / toluene / 2 h / 70 °C / Cooling with ice 4: hydrogenchloride / ethanol View Scheme

: 131028-55-2
[2-(4-Chloromethyl-phenoxy)-ethyl]-dimethyl-amine

: 122892-31-3
N-<4-<2-(dimethylamino)ethoxy>benzyl>-3,4-dimethoxybenzamide hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonium hydroxide / methanol / 6 h / 80 °C / Autoclave 2: N-ethyl-N,N-diisopropylamine / toluene / 2 h / 70 °C / Cooling with ice 3: hydrogenchloride / ethanol View Scheme

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Chemistry

IUPAC Name: N-[[4-(2-Dimethylaminoethyloxy)phenyl]methyl]-3,4-dimethoxybenzamide hydrochloride
CAS: 122892-31-3
Formula: C₂₀H₂₇ClN₂O₄
Molecular Weight: 394.89
Molecular Structure of N-[[4-(2-Dimethylaminoethyloxy)phenyl]methyl]-3,4-dimethoxybenzamide hydrochloride (122892-31-3 ):

Flash Point: 262.3 °C
Melting Point: 194-195 °C
Boiling Point: 510.1 °C at 760 mmHg
Vapour Pressure: 1.6E-10 mmHg at 25°C
Appearance: Crystalline Solid
Enthalpy of Vaporization: 78.08 kJ/mol
The classification of N-[[4-(2-Dimethylaminoethyloxy)phenyl]methyl]-3,4-dimethoxybenzamide hydrochloride (122892-31-3) are Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals;Itopride.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
dog	LD50	oral	600mg/kg (600mg/kg)	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 740, 1995.
mouse	LD50	intravenous	164mg/kg (164mg/kg)	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 740, 1995.
mouse	LD50	oral	> 2gm/kg (2000mg/kg)	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 740, 1995.
rat	LD50	intravenous	275mg/kg (275mg/kg)	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 740, 1995.
rat	LD50	oral	> 2gm/kg (2000mg/kg)	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 740, 1995.

Specification

The chemical synonyms of N-[[4-(2-Dimethylaminoethyloxy)phenyl]methyl]-3,4-dimethoxybenzamide hydrochloride (122892-31-3) are N-((4-(2-(Dimethylamino)ethoxy)phenyl)methyl)-3,4-dimethoxybenzamidemonohydr ; N-((4-(2-(Dimethylamino)ethoxy)phenyl)methyl)-3,4-dimethoxy-benzamidmonohy ; N-((4-(2-(Dimethylamino)ethoxy)phenyl)methyl)-3,4-dimethoxy-benzamidmonohydrochloride ; N-(4-(2-(Dimethylamino)ethoxy)benzyl)-3,4-dimethoxidebenzamidehydrochloride .The product of N-[[4-(2-Dimethylaminoethyloxy)phenyl]methyl]-3,4-dimethoxybenzamide hydrochloride (122892-31-3 ) can enhance Dopamine D2-receptor antagonist with anticholinesterase activity. Gastroprokinetic.