122898-67-3

Basic information

• Product Name: Itopride
• Synonyms: n-[[4-(2-dimethylaminoethoxy)phenyl]methyl]-3,4-dimethoxy-benzamide;ITOPRIDE;ITOPRIDE HYDROCHLORIDE 98-102%;2-ETHOXY-5-ETHYL-N-((1-ETHYLPYRROLIDIN-2-YL)METHYL)-6-HYDROXY-3-IODOBENZAMIDE HYDROCHLORIDE;3,4-Dimethoxy-N-[4-[2-(dimethylamino)ethoxy]benzyl]benzamide;N-[4-[2-(Dimethylamino)ethoxy]benzyl]-3,4-dimethoxybenzene-1-carboxamide;N-[[4-(2-dimethylaminoethyloxy)phenyl]methyl]-3,4-dimethoxybenzamide;N-[[4-(2-dimethylaminoethyloxy)phenyl]methyl]-3,4-dimethoxy-benzamide
• CAS NO: 122898-67-3
• Molecular Formula: C₂₀H₂₆N₂O₄
• Molecular Weight: 358.43
• EINECS: 1312995-182-4
• Mol File: 122898-67-3.mol

Chemical Properties

• Melting Point: 111-112°
• Boiling Point: 510.121 °C at 760 mmHg
• Flash Point: 262.312 °C
• Appearance: white
• Density: 1.123 g/cm³
• Vapor Pressure: 1.6E-10mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: 2-8°C
• PKA: 13.98±0.46(Predicted)
• CAS DataBase Reference: Itopride(CAS DataBase Reference)
• NIST Chemistry Reference: Itopride(122898-67-3)
• EPA Substance Registry System: Itopride(122898-67-3)

Safety Data

• Hazardous Substances Data: 122898-67-3(Hazardous Substances Data)

Usage

Uses

dyspepsia therapy

InChI:InChI=1/C20H26N2O4/c1-22(2)11-12-26-17-8-5-15(6-9-17)14-21-20(23)16-7-10-18(24-3)19(13-16)25-4/h5-10,13H,11-12,14H2,1-4H3,(H,21,23)

Upstream product

• 20059-73-8 4-<2-(dimethylamino)ethoxy>benzylamine 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 943518-63-6 N-(4-hydroxybenzyl)-3,4-dimethoxybenzamide 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 1228693-36-4 C₃₁H₃₁F₁₇N₂O₅ 
• 201230-82-2 carbon monoxide 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 108-95-2 phenol 
• 13468-02-5 dimethyl(2-phenoxyethyl)amine 
• 131028-55-2 [2-(4-Chloromethyl-phenoxy)-ethyl]-dimethyl-amine 
• 2024-83-1 veratronitrile 
• 106-44-5 p-cresol 
• 51344-14-0 N,N-dimethyl-2-<4-methylphenoxy>-ethylamine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

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

Relevant articles and documents

Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous-Flow

Phosphine-mediated deoxygenative nucleophilic substitutions, such as the Mitsunobu reaction, are of great importance in organic synthesis. However, the conventional protocols require stoichiometric oxidants to trigger the formation of the oxyphosphonium i

Near-Ambient-Temperature Dehydrogenative Synthesis of the Amide Bond: Mechanistic Insight and Applications

The current existing methods for the amide bond synthesis via acceptorless dehydrogenative coupling of amines and alcohols all require high reaction temperatures for effective catalysis, typically involving reflux in toluene, limiting their potential practical applications. Herein, we report a system for this reaction that proceeds under mild conditions (reflux in diethyl ether, boiling point 34.6 °C) using ruthenium PNNH complexes. The low-temperature activity stems from the ability of Ru-PNNH complexes to activate alcohol and hemiaminals at near-ambient temperatures through the assistance of the terminal N-H proton. Mechanistic studies reveal the presence of an unexpected aldehyde-bound ruthenium species during the reaction, which is also the catalytic resting state. We further utilize the low-temperature activity to synthesize several simple amide bond-containing commercially available pharmaceutical drugs from the corresponding amines and alcohols via the dehydrogenative coupling method.

Manganese Catalyzed Direct Amidation of Esters with Amines

The transition metal catalyzed amide bond forming reaction of esters with amines has been developed as an advanced approach for overcoming the shortcomings of traditional methods. The broad scope of substrates in transition metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines, and secondary alkyl amines to form amides. It is noteworthy that this approach provides the first example of the transition metal catalyzed amide bond forming reaction from fatty acid esters and amines. The acid-base mechanism for the manganese(I)-catalyzed direct amidation of esters with amines was elucidated by DFT calculations.

Preparation method of itopride hydrochloride

The invention relates to a preparation method of itopride hydrochloride and belongs to the technical field of raw material preparation. The technical scheme is as follows: the preparation method of itopride hydrochloride comprises the steps as follows: an intermediate I is prepared from initial materials including 3,4-dimethoxybenzamide, formaldehyde and phenol with a one-pot method; the intermediate I and N,N-dimethyl chloroethane hydrochloride are subjected to a substitution reaction to produce an intermediate II; finally, itopride hydrochloride is prepared through salification. The itopridepreparation process comprises a short and convenient route and is economical and environmentally friendly.

method for preparing itopride using micro flow reactor

The present invention relates to a method for preparing itopride by using a micro flow reactor, wherein the yield and the degree of purity of the itopride generated by using the micro flow reactor can be improved; thionyl chloride or oxalyl chloride can be safely used; and leakage of noxious gases, such as a sulfur dioxide gas and/or a hydrochloric acid gas can be prevented. Also, the itopride can be manufactured through a simple process without an extra separation and purification process of an intermediate product that is generated during manufacturing.

Fe(ClO 4) 3 ·h 2 O-Catalyzed Ritter Reaction: A Convenient Synthesis of Amides from Esters and Nitriles

An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with esters catalyzed by Fe(ClO 4) 3 ·H 2 O is described. Fe(ClO 4) 3 ·H 2 O is an economically efficient catalyst for the Ritter reaction under solvent-free conditions. Reactions of a range of esters (benzyl, sec-alkyl, and tert-butyl esters) with nitriles (primary, secondary, tertiary, and aryl nitriles) were performed to provide the corresponding amides in high to excellent yields.

Nickel-Catalyzed Phosphine Free Direct N-Alkylation of Amides with Alcohols

Herein, we developed an operational simple, practical, and selective Ni-catalyzed synthesis of secondary amides. Application of renewable alcohols, earth-abundant and nonprecious nickel catalyst facilitates the transformations, releasing water as byproduct. The catalytic system is tolerant to a variety of functional groups including nitrile, allylic ether, and alkene and could be extended to the synthesis of bis-amide, antiemetic drug Tigan, and dopamine D2 receptor antagonist Itopride. Preliminary mechanistic studies revealed the participation of a benzylic C-H bond in the rate-determining step.

Preparation method of medicine of itopride hydrochloride for promoting gastrointestinal motility

The invention discloses a preparation method of medicine of itopride hydrochloride for promoting gastrointestinal motility. The method comprises the following steps that p-hydroxy methylbenzene is used as a raw material to take a reaction with dimethylaminoethyl chloride hydrochloride; then, 4-(2-dimethylamino oxethyl) benzyl bromide is synthesized through bromination; next, the 4-(2-dimethylamino oxethyl) benzyl bromide and 3,4-dimethoxybenzonitrile take a reaction to obtain a product of itopride under the solvent-free condition through copper trifluoromethanesulfonate catalysis. The preparation method has the advantages a bran-new synthesis route is provided; the itopride is synthesized through Ritter reaction under the solvent-free condition; the advantage of green and environment-friendly effects is realized; meanwhile, the used raw material resources are wide and sufficient; the price is low; the reaction conditions are mild.

Preparation method of itopride hydrochloride

The invention relates to a preparation method of itopride hydrochloride. The preparation method includes: using 2-dimethylaminoethyl chloride hydrochloride and phenol as starting materials for reaction; subjecting the starting materials to etherification, chloromethylation, amino substitution, amidation and salifying to obtain itopride hydrochloride. Chloromethylation promoted by C/CHO is adopted, so that a step of imine reduction is omitted, solid residue generated by a reductant is eliminated, and reaction safety is improved; raw materials used in the method are low in price, sufficient in market supply and easy to purchase; reaction in each step is classic, and the preparation method is safe, easy to control and suitable for industrial production.

SYSTEM PROVIDING CONTROLLED DELIVERY OF GASEOUS CO FOR CARBONYLATION REACTIONS

A carbonylation system comprising at least one carbon monoxide producing chamber and at least one carbon monoxide consuming chamber forming an interconnected multi-chamber system, said interconnection allowing carbon monoxide to pass from the at least one carbon monoxide producing chamber to the at least one carbon monoxide consuming chamber, said at least one carbon monoxide producing chamber containing a reaction mixture comprising a carbon monoxide precursor and a catalyst, said at least one carbon monoxide consuming chamber being suitable for carbonylation reactions, said interconnected multi- chamber system being sealable from the surrounding atmosphere during carbonylation.