Trimethobenzamide hydrochloride

Base Information

• Chemical Name: Trimethobenzamide hydrochloride
• CAS No.: 554-92-7
• Molecular Formula: C21H29ClN2O5
• Molecular Weight: 424.925
• Hs Code.: 2924296000
• European Community (EC) Number: 209-075-6
• NSC Number: 757359,37882
• UNII: WDQ5P1SX7Q
• DSSTox Substance ID: DTXSID7047774
• Wikidata: Q27292581
• NCI Thesaurus Code: C29522
• RXCUI: 57227
• ChEMBL ID: CHEMBL1200887
• Mol file: 554-92-7.mol

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

Chemical Property of Trimethobenzamide hydrochloride

Chemical Property:

• Melting Point: 187.5-190°
• Boiling Point: 506.9 °C at 760 mmHg
• Flash Point: 260.4 °C
• PSA: 69.26000
• Density: 1.131 g/cm³
• LogP: 3.77570
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 424.1764997
• Heavy Atom Count: 29
• Complexity: 440

Purity/Quality:

99%, ^*data from raw suppliers

Trimethobenzamide Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)CCOC1=CC=C(C=C1)CNC(=O)C2=CC(=C(C(=C2)OC)OC)OC.Cl
• Recent ClinicalTrials: A Study to Investigate the Safety, Tolerability, and Pharmacokinetics of PF-06649751 in Subjects With Idiopathic Parkinson's Disease
• General Description: Trimethobenzamide hydrochloride is an antiemetic agent used to treat nausea and vomiting. An improved synthesis method has been developed to enhance its purity and yield by utilizing N,N'-carbonyldiimidazole (CDI) as a coupling reagent, avoiding common impurities and eliminating the need for extensive purification steps. The optimized process results in a high-purity product (≥99.5%) with efficient production.

Technology Process of Trimethobenzamide hydrochloride

There total 6 articles about Trimethobenzamide hydrochloride 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:

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → N-[p-[(2-dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide hydrochloride (554-92-7)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium carbonate / butanone / 18 h / 25 - 80 °C / Large scale

2: ammonia / methanol / 8 h / 50 - 55 °C / 6000.6 - 7500.75 Torr / Large scale

3: potassium carbonate / ethyl acetate / 2.5 h / 10 °C / Inert atmosphere; Large scale

4: hydrogenchloride / acetone; water / Large scale

With hydrogenchloride; ammonia; sodium carbonate; potassium carbonate; In methanol; water; ethyl acetate; acetone; butanone;

DOI:10.1021/op400113a

Reference yield:

4-(2-dimethylaminoethoxy)benzaldehyde (15182-92-0,87330-48-1) → N-[p-[(2-dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide hydrochloride (554-92-7)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonia / methanol / 8 h / 50 - 55 °C / 6000.6 - 7500.75 Torr / Large scale

2: potassium carbonate / ethyl acetate / 2.5 h / 10 °C / Inert atmosphere; Large scale

3: hydrogenchloride / acetone; water / Large scale

With hydrogenchloride; ammonia; potassium carbonate; In methanol; water; ethyl acetate; acetone;

DOI:10.1021/op400113a

Reference yield:

Trimethobenzamide (138-56-7) → N-[p-[(2-dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide hydrochloride (554-92-7)

Guidance literature:

With hydrogenchloride; In water; acetone; Large scale;

DOI:10.1021/op400113a

upstream raw materials:

Trimethobenzamide

4-hydroxy-benzaldehyde

4-(2-dimethylaminoethoxy)benzaldehyde

4-<2-(dimethylamino)ethoxy>benzylamine

Refernces

An improved process for trimethobenzamide hydrochloride

10.1021/op400113a

The study details an enhanced method for synthesizing trimethobenzamide hydrochloride (Ia), an antiemetic agent used to treat nausea. The researchers aimed to develop a process that avoids common impurities formed during the coupling of 4-(2-dimethylaminoethoxy)benzyl amine (IV) with 3,4,5-trimethoxy benzoic acid (V). They experimented with various coupling reagents and found that N,N'-carbonyldiimidazole (CDI) provided the best results. By optimizing the mole equivalents of CDI, they achieved a high-purity product without the need for column chromatography or repeated crystallization. The final process involved reacting 3,4,5-trimethoxy benzoic acid with CDI to form an intermediate, which was then coupled with 4-(2-dimethylaminoethoxy)benzyl amine in the presence of potassium carbonate, yielding trimethobenzamide hydrochloride with a purity of =99.5% and a satisfactory yield.

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