Trimethobenzamide

Base Information

• Chemical Name: Trimethobenzamide
• CAS No.: 138-56-7
• Molecular Formula: C21H28N2O5
• Molecular Weight: 388.464
• Hs Code.: 2924299090
• European Community (EC) Number: 205-332-1
• UNII: W2X096QY97
• DSSTox Substance ID: DTXSID8023711
• Nikkaji Number: J5.636G
• Wikipedia: Trimethobenzamide
• Wikidata: Q7842199
• NCI Thesaurus Code: C61989
• RXCUI: 38685
• Metabolomics Workbench ID: 42979
• ChEMBL ID: CHEMBL1201256
• Mol file: 138-56-7.mol

Synonyms:T-Gen;Tebamide;Ticon;Tigan;trimethobenzamide;trimethobenzamide monohydrochloride

Chemical Property of Trimethobenzamide

Chemical Property:

• Vapor Pressure: 2.13E-10mmHg at 25°C
• Boiling Point: 506.9 °C at 760 mmHg
• PKA: pKa 8.27±0.03(H2O) (Uncertain)
• Flash Point: 260.4 °C
• PSA: 69.26000
• Density: 1.131 g/cm³
• LogP: 2.97370
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 388.19982200
• Heavy Atom Count: 28
• Complexity: 440

Purity/Quality:

99% ^*data from raw suppliers

N-(4-(2-(Dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxybenzamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Gastrointestinal Agents
• Canonical SMILES: CN(C)CCOC1=CC=C(C=C1)CNC(=O)C2=CC(=C(C(=C2)OC)OC)OC
• Recent ClinicalTrials: Apokyn for Motor IMProvement of Morning AKinesia Trial (AM IMPAKT)
• Uses: Antiemetic.
• Therapeutic Function: Antinauseant

Technology Process of Trimethobenzamide

There total 16 articles about Trimethobenzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

5-iodo-1,2,3-trimethoxybenzene (25245-29-8) + carbon monoxide (201230-82-2) + 4-<2-(dimethylamino)ethoxy>benzylamine (20059-73-8) → Trimethobenzamide (138-56-7)

Guidance literature:

With triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; at 80 ℃; for 18h; Glovebox; Sealed tube; Inert atmosphere;

DOI:10.1021/ja502911e

Reference yield: 94.0%

(3,4,5-trimethoxyphenyl)methanol (3840-31-1) + 4-<2-(dimethylamino)ethoxy>benzylamine (20059-73-8) → Trimethobenzamide (138-56-7)

Guidance literature:

With potassium tert-butylate; [Ru(P^tBuNNH^Bn)H(CO)Cl]; In tert-butyl methyl ether; at 70 ℃; for 60h; under 760.051 Torr; Inert atmosphere;

DOI:10.1021/acscatal.1c00728

Reference yield: 94.0%

4-<2-(dimethylamino)ethoxy>benzylamine (20059-73-8) + tert-butyl phenyl(3,4,5-trimethoxybenzoyl)carbamate → Trimethobenzamide (138-56-7)

Guidance literature:

In acetonitrile; at 20 ℃; for 15h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.9b02013

upstream raw materials:

4-<2-(dimethylamino)ethoxy>benzylamine

3,4,5-Trimethoxybenzoyl chloride

Eudesmic acid

4-(2-dimethylaminoethoxy)benzaldehyde

Downstream raw materials:

N-[p-[(2-dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide hydrochloride

Refernces

• 1、 Rahman, Md. Mahbubur,Li, Guangchen,Szostak, Michal. "Metal-Free Transamidation of Secondary Amides by N-C Cleavage". . p. 12091 - 12100. Retrieved 2019/10/11.
• 2、 -. "REDOX DEHYDRATION COUPLING CATALYSTS AND METHODS RELATED THERETO". Page/Page column 17. . Retrieved 2017/08/01.