Product Name

  • Name

    Itopride hydrochloride

  • EINECS 602-905-1
  • CAS No. 122892-31-3
  • Article Data10
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point 194-195 °C
  • Formula C20H26N2O4.HCl
  • Boiling Point 510.1 °C at 760 mmHg
  • Molecular Weight 394.898
  • Flash Point 262.3 °C
  • Transport Information
  • Appearance white or pale brownish crystal
  • Safety 61
  • Risk Codes 50
  • Molecular Structure Molecular Structure of 122892-31-3 (Itopride hydrochloride)
  • Hazard Symbols N
  • Synonyms Benzamide,N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4-dimethoxy-, monohydrochloride(9CI);Ganaton;HSR 803;
  • PSA 60.03000
  • LogP 3.76710

Synthetic route

itopride
122898-67-3

itopride

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

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

Conditions
ConditionsYield
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 ethanol90%
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%
veratronitrile
2024-83-1

veratronitrile

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

(4-(2-(dimethylamino)ethoxy)phenyl)methanol

itopride
122898-67-3

itopride

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

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

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

N-(4-hydroxybenzyl)-3,4-dimethoxybenzamide

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

2-(dimethylamino)ethyl chloride

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

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

Conditions
ConditionsYield
With potassium iodide In N,N-dimethyl-formamide at 130 - 135℃; Temperature;87%
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

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

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

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

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

Conditions
ConditionsYield
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%
4-cyanophenol
767-00-0

4-cyanophenol

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

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

Conditions
ConditionsYield
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
4-cyanophenyl mesylate
138373-10-1

4-cyanophenyl mesylate

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

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

Conditions
ConditionsYield
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
(4-methanesulfonyloxyphenylmethane)amine
1052148-15-8

(4-methanesulfonyloxyphenylmethane)amine

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

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

Conditions
ConditionsYield
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
phenol
108-95-2

phenol

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

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

Conditions
ConditionsYield
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
dimethyl(2-phenoxyethyl)amine
13468-02-5

dimethyl(2-phenoxyethyl)amine

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

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

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

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

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

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

Conditions
ConditionsYield
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
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate; triethylamine / N,N-dimethyl-formamide / 2 h / 80 °C
2.1: methanol; sodium tetrahydroborate / Cooling with ice
3.1: trifluorormethanesulfonic acid / toluene / 8 h / 80 °C
3.2: 0 °C
View Scheme
p-cresol
106-44-5

p-cresol

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine; potassium hydroxide / di-isopropyl ether; N,N-dimethyl-formamide / 2 h / 80 °C
2: N-Bromosuccinimide / chloroform / 5 h / Reflux
3: copper(II) bis(trifluoromethanesulfonate) / 5 h / 100 °C
4: hydrogenchloride / ethanol / 0 °C
View Scheme
N,N-dimethyl-2-<4-methylphenoxy>-ethylamine
51344-14-0

N,N-dimethyl-2-<4-methylphenoxy>-ethylamine

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-Bromosuccinimide / chloroform / 5 h / Reflux
2: copper(II) bis(trifluoromethanesulfonate) / 5 h / 100 °C
3: hydrogenchloride / ethanol / 0 °C
View Scheme
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydroxylamine hydrochloride / ethanol / Reflux
1.2: 6 h / Reflux
2.1: copper(II) bis(trifluoromethanesulfonate) / 5 h / 100 °C
3.1: hydrogenchloride / ethanol / 0 °C
View Scheme

Itopride hydrochloride Chemical Properties

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. 

Itopride hydrochloride Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect 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.

Itopride hydrochloride 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.

 

 


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