Lerisetron

Base Information

• Chemical Name: Lerisetron
• CAS No.: 143257-98-1
• Molecular Formula: C18H20 N4
• Molecular Weight: 292.384
• European Community (EC) Number: 852-556-6
• UNII: Q36R82SXRG
• DSSTox Substance ID: DTXSID90162368
• Nikkaji Number: J550.685I
• Wikipedia: Lerisetron
• Wikidata: Q6528811
• NCI Thesaurus Code: C30143
• Pharos Ligand ID: FB3HUZ6RMM6P
• Metabolomics Workbench ID: 153847
• ChEMBL ID: CHEMBL56900
• Mol file: 143257-98-1.mol

Synonyms:1-benzyl-2-(1-piperazinyl)benzimidazole;lerisetron

Chemical Property of Lerisetron

Chemical Property:

• Vapor Pressure: 3.31E-10mmHg at 25°C
• Boiling Point: 502°Cat760mmHg
• Flash Point: 257.4°C
• PSA: 33.09000
• Density: 1.22g/cm³
• LogP: 2.88800
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 292.16879665
• Heavy Atom Count: 22
• Complexity: 349

Purity/Quality:

98% ^*data from raw suppliers

1-Benzyl-2-piperazin-1-yl-1H-benzimidazole dihydrochloride 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1)C2=NC3=CC=CC=C3N2CC4=CC=CC=C4
• Recent ClinicalTrials: Lerisetron Compared With Granisetron in Preventing Nausea and Vomiting in Men Being Treated With Radiation Therapy for Stage I Seminoma

Technology Process of Lerisetron

There total 5 articles about Lerisetron 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: 98.0%

tert-butyl-4-(1-benzyl-1H-benzo[d]imidazol-2-yl)piperazine-1-carboxylate → 4-(1-benzyl-1H-benzo[d]imidazol-2-yl)piperazin-1-ium chloride (143257-98-1)

Guidance literature:

With hydrogenchloride; In diethyl ether; at 20 ℃;

DOI:10.1002/anie.201311029

Reference yield: 95.0%

piperazine (110-85-0) + 1-benzyl-2-chlorobenzimidazole (43181-78-8) → lerisetron (143257-98-1)

Guidance literature:

at 150 - 160 ℃; for 0.5h;

DOI:10.1021/jm960442e

Reference yield:

2-chloro-1H-benzoimidazole (4857-06-1) → lerisetron (143257-98-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 1 h / 20 °C

1.2: dimethylformamide / Heating

2.1: 150 °C

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00417-6

upstream raw materials:

piperazine

1-benzyl-2-chlorobenzimidazole

2-chloro-1H-benzoimidazole

benzyl bromide

Downstream raw materials:

9-{4-[4-(1-benzyl-1H-benzimidazol-2-yl)-piperazin-1-yl]-butyl}-9H-fluorene-9-carboxylic Acid-(2.2,2-trifluoro-ethyl)-amide

Refernces

• 1、 Parihar, Harish S.,Suryanarayanan, Asha,Ma, Chun,Joshi, Prasad,Venkataraman, Padma,Schulte, Marvin K.,Kirschbaum, Karen S.. "5-HT3R binding of lerisetron: An interdisciplinary approach to drug-receptor interactions". . p. 2133 - 2136. Retrieved 2007/10/03.
• 2、 Orjales, Aurelio,Mosquera, Ramón,Labeaga, Luis,Rodes, Rosa. "New 2-piperazinylbenzimidazole derivatives as 5-HT3 antagonists. Synthesis and pharmacological evaluation". . p. 586 - 593. Retrieved 2007/10/03.