20662-53-7

Basic information

• Product Name: 4-(2-KETO-1-BENZIMIDAZOLINYL)PIPERIDINE
• Synonyms: 4-(2-Keto-1-benzimidazolinyl)piperidine,97%;1-(Piperidin-4-yl)-1,3-dihydrobenzoimidazol-2-one;1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one;1,3-Dihydro-1-(piperidin-4-yl)-2H-benzimidazol-2-one;2H-BenziMidazol-2-one, 1,3-dihydro-1-(4-piperidinyl)-;1,3-Dihydro-1-(4-piperidinyl)benziMidazol-2-one;4-(2-Oxo-1,3-dihydro- benziMidazol-1-yl)piperidine;4-(2-Oxo-1-benziMidazolinyl)piperidine
• CAS NO: 20662-53-7
• Molecular Formula: C₁₂H₁₅N₃O
• Molecular Weight: 217.27
• EINECS: 243-950-3
• Product Categories: Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Benzimidazoles;Building Blocks;Heterocyclic Building Blocks
• Mol File: 20662-53-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 183-185 °C(lit.)
• Boiling Point: 357.82°C (rough estimate)
• Appearance: Off-white to slightly yellow/Powder
• Density: 1.1005 (rough estimate)
• Refractive Index: 1.5290 (estimate)
• PKA: 12.06±0.30(Predicted)
• CAS DataBase Reference: 4-(2-KETO-1-BENZIMIDAZOLINYL)PIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-KETO-1-BENZIMIDAZOLINYL)PIPERIDINE(20662-53-7)
• EPA Substance Registry System: 4-(2-KETO-1-BENZIMIDAZOLINYL)PIPERIDINE(20662-53-7)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-36-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 20662-53-7(Hazardous Substances Data)

Usage

Chemical Properties

off-white to slightly yellow powder

Uses

4-(2-Keto-1-benzimidazolinyl)piperidine was used to study the structure–activity relationships with several potent and selective analogues.

InChI:InChI=1/C12H15N3O/c16-12-14-10-3-1-2-4-11(10)15(12)9-5-7-13-8-6-9/h1-4,9,13H,5-8H2,(H,14,16)/p+1

Upstream product

• 53786-47-3 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-piperidine-1-carboxylic acid ethyl ester 
• 1493-27-2 ortho-nitrofluorobenzene 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 95-54-5 1,2-diamino-benzene 
• 79099-00-6 tert‐butyl 4‐((2‐aminophenyl)amino)piperidine‐1‐carboxylate 
• 58859-46-4 ethyl 4-aminopiperidine-1-carboxylate 
• 87120-73-8 tert‐butyl 4‐((2‐nitrophenyl)amino)piperidine‐1‐carboxylate 
• 87120-72-7 1-(tert-butoxycarbonyl)-4-aminopiperidine 
• 173843-48-6 4-(3-Methyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboxylicacid tert-butyl ester 
• 87120-77-2 ethyl 4-((2-aminophenyl)amino)piperidine-1-carboxylate 
• 85443-52-3 ethyl 4-((2-nitrophenyl)amino)piperidine-1-carboxylate 
• 87120-81-8 1,3-dihydro-1-(1-tert-butyloxycarbonylpiperidin-4-yl)-2H-benzimidazol-2-one 

Downstream Products

• 109758-38-5 1-{1-[3-(2-Oxo-6-phenyl-piperidin-1-yl)-propyl]-piperidin-4-yl}-1,3-dihydro-benzoimidazol-2-one; compound with oxalic acid 
• 61220-24-4 1-[1-(2-indol-3-yl-ethyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one 
• 130965-67-2 5-[2-(4-(2-oxo-benzimidazolinyl)piperidinyl)ethyl]-4-(4-fluorophenyl)-1,3-dihydro-2H-imidazol-2-one 
• 57381-98-3 1-{1-[3-(2-chloro-4-fluoro-phenoxy)-propyl]-piperidin-4-yl}-1,3-dihydro-benzoimidazol-2-one 
• 63004-55-7 N-{2-[4-(2,3-dihydro-2-oxo-1-benzimidazol-1-yl)-1-piperidinyl] ethyl}-2-nitrobenzamide hydrochloride 
• 61317-26-8 1-{1-[4,4-bis-(4-fluoro-phenyl)-cyclohexyl]-piperidin-4-yl}-1,3-dihydro-benzoimidazol-2-one 
• 61300-24-1 1-[1-(4,4-diphenyl-cyclohexyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one 
• 74971-66-7 methyl 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)piperidino]ethyl]benzoate hydrochloride 
• 2062-78-4 pimozide 
• 16148-06-4 R 4782 

Relevant articles and documents

Novel BQCA- and TBPB-Derived M1 Receptor Hybrid Ligands: Orthosteric Carbachol Differentially Regulates Partial Agonism

Recently, investigations of the complex mechanisms of allostery have led to a deeper understanding of G protein-coupled receptor (GPCR) activation and signaling processes. In this context, muscarinic acetylcholine receptors (mAChRs) are highly relevant due to their exemplary role in the study of allosteric modulation. In this work, we compare and discuss two sets of putatively dualsteric ligands, which were designed to connect carbachol to different types of allosteric ligands. We chose derivatives of TBPB [1-(1′-(2-tolyl)-1,4′-bipiperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one] as M1-selective putative bitopic ligands, and derivatives of benzyl quinolone carboxylic acid (BQCA) as an M1 positive allosteric modulator, varying the distance between the allosteric and orthosteric building blocks. Luciferase protein complementation assays demonstrated that linker length must be carefully chosen to yield either agonist or antagonist behavior. These findings may help to design biased signaling and/or different extents of efficacy.

The preparation method of the deuterium generation of Mauzy is special

The invention discloses a preparation method of deuterated pimozide. The pimozide-d4 is synthesized from 4-bromopentafluorobenzene-d4 through eight steps. The provided preparation method has the advantages of reasonable technological design, simple operation, easy product separation and purification, easily-available raw materials, high yield, and high purity. The isotope abundance of the obtained target product is high. The prepared stable isotope-labeled pimozide-d4 can be well applied to clinical pharmacokinetics researches, so people can acknowledge the metabolism process and action mechanism of pimozide in human body more precisely and conveniently, and thus the deuterated pimozide has an important application value.

Concise and simple synthesis of M1 allosteric agonist TBPB

A concise and simple synthesis of M1 allosteric agonist 1-(1′-(2-methylbenzyl)-1,4′-bipiperidin-4-yl)-1H-benzo[d] imidazol-2(3H)-one (TBPB) using economical and commercially available orthophenylenediamine (O-PDA) and Boc piperidone has been described. The disclosed scheme allows synthesizing more analogs that were otherwise difficult to prepare with the original method. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.