5-Chloro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Base Information

• Chemical Name: 5-Chloro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one
• CAS No.: 53786-28-0
• Molecular Formula: C12H14ClN3O
• Molecular Weight: 251.716
• Hs Code.: 29339980
• European Community (EC) Number: 258-771-6
• UNII: 53TAT94YDS
• DSSTox Substance ID: DTXSID4057764
• Nikkaji Number: J279.500K
• Wikidata: Q72457899
• ChEMBL ID: CHEMBL3189082
• Mol file: 53786-28-0.mol

Synonyms:53786-28-0;5-Chloro-1-(4-piperidyl)-2-benzimidazolinone;5-Chloro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one;1-(4-Piperidinyl)-1,3-dihydro-5-chlorobenzimidazolone;6-chloro-3-piperidin-4-yl-1H-benzimidazol-2-one;DOMPERIDONE IMPURITY A;5-Chloro-1-piperidin-4-yl-1,3-dihydro-2H-benzimidazol-2-one;5-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one;EINECS 258-771-6;5-Chloro-1-(4-piperidinyl)-2-benzimidazolinone;2H-Benzimidazol-2-one, 5-chloro-1,3-dihydro-1-(4-piperidinyl)-;5-chloro-1-(piperidin-4-yl)-1,3-dihydro-2h-benzimidazol-2-one;53TAT94YDS;DTXSID4057764;5-CHLORO-1-PIPERIDIN-4-YL-1,3-DIHYDRO-BENZOIMIDAZOL-2-ONE;R-29676;5-Chloro-1-(4-piperidyl)-1H-benzimidazol-2(3H)-one;5-CHLORO-1-(PIPERIDIN-4-YL)-2,3-DIHYDRO-1H-1,3-BENZODIAZOL-2-ONE;DoMperidone EP IMpurity A;UNII-53TAT94YDS;SCHEMBL655853;CHEMBL3189082;DTXCID5031553;SCHEMBL22588043;AMY40896;BCP34405;STR08979;Tox21_113838;MFCD02093793;AKOS015888111;AB10845;GF-0121;NCGC00253719-01;AC-18949;CAS-53786-28-0;C3068;CS-0155747;FT-0640191;1-(4-piperidyl)-5-chloro-2-benzimidazolinone;R29676;1-(4-piperidyl)-5-chloro-benzimidazolin-2-one;4-(5-chloro-2-oxo-1-benzimidazolinyl)piperidine;4-(5-Chlorobenzimidazol-2-on-1-yl)-piperidine;5-chloro-1-(4-piperidyl)- 2-benzimidazolinone;SR-01000945186;SR-01000945186-1;5-Chloro-1-(4-piperidyl)-2-benzimidazolinone, 97%;5-CHLORO-1-(4-PIPERIDINYL)-2-BENZIMIDAZOLIDINONE;5-chloro-1-dihydro-1-(4-piperidinyl)-2h-benzimidazole-2-one;4-(6-CHLORO-1,2-DIHYDRO-2-OXOBENZO(D)IMIDAZOL-3-YL)PIPERIDINE;5-Chloro 1,3 dihydro -1- (4-piperidinyl) -2H- benzimidazol - 2 -one;5-CHLORO-1,3-DIHYDRO-1-(PIPERIDIN-4-YL)-2H-BENZIMIDAZOL-2-ONE;5-CHLORO-1-(4-PIPERIDINYL)-1,3-DIHYDRO-2H-BENZIMIDAZOL-2-ONE

Chemical Property of 5-Chloro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Chemical Property:

• Vapor Pressure: 0Pa at 20℃
• Melting Point: 228-231 °C(lit.)
• Refractive Index: 1.605
• PKA: 11.12±0.30(Predicted)
• PSA: 49.82000
• Density: 1.323 g/cm³
• LogP: 2.23630
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 549mg/L at 20℃
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 251.0825398
• Heavy Atom Count: 17
• Complexity: 306

Purity/Quality:

99.9% ^*data from raw suppliers

1-(4-Piperidinyl)-1,3-dihydro-5-chlorobenzimidazolone 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCCC1N2C3=C(C=C(C=C3)Cl)NC2=O
• Uses: 5-Chloro-1-(4-piperidyl)-2-benzimidazolinone is a metabolite of the gastrokinetic and antinauseant drug Domperidone (D531100). 5-Chloro-1-(4-piperidinyl)-2-benzimidazolidinone (Domperidone EP Impurity A) is a metabolite of the gastrokinetic and antinauseant drug Domperidone (D531100).

Technology Process of 5-Chloro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

There total 12 articles about 5-Chloro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one 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: 96.0%

4-(5-chloro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboxylic acid ethyl ester (53786-46-2) → 5-chloro-1-(piperidin-4-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one (53786-28-0)

Guidance literature:

With sodium hydroxide; for 8h; Heating;

DOI:10.1021/jm00388a012

Reference yield:

4-(4-chloro-2-nitro-anilino)-piperidine-1-carboxylic acid ethyl ester (53786-44-0) → 5-chloro-1-(piperidin-4-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one (53786-28-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Zn; aq. HCl / methanol / 50 °C

2: acetonitrile

3: aq. NaOH / 100 °C

With hydrogenchloride; sodium hydroxide; zinc; In methanol; acetonitrile;

DOI:10.1016/j.bmcl.2006.07.044

Reference yield:

ethyl 4-aminopiperidine-1-carboxylate (58859-46-4) → 5-chloro-1-(piperidin-4-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one (53786-28-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / Na₂CO₃, KI / various solvent(s) / 28 h / 160 °C

2: 93 percent / H₂ / Raney Ni / ethanol; tetrahydrofuran / 1 h / Ambient temperature

3: 90 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: 96 percent / 10percent NaOH / 8 h / Heating

With sodium hydroxide; hydrogen; sodium carbonate; triethylamine; potassium iodide; nickel; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jm00388a012

upstream raw materials:

4-(5-chloro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboxylic acid ethyl ester

ethyl 4-aminopiperidine-1-carboxylate

ethyl 4-[(2-amino-4-chlorophenyl)amino]piperidine-1-carboxylate

4-(4-chloro-2-nitro-anilino)-piperidine-1-carboxylic acid ethyl ester

Downstream raw materials:

1-[1-(4-(4-fluorophenyl)-tetrahydro-2-furylmethyl)-4-piperidyl]-5-chloro-benzimidazolin-2-one maleate

domperidone

7-(4-(6-chloro-1,2-dihydro-2-oxobenzo[d]imidazol-3-yl)piperidin-1-yl)-1-(2,4-difluorophenyl)-1,4-dihydro-8-methyl-6-nitro-4-oxoquinoline-3-carboxylic acid

C₂₅H₂₈ClF₃N₄O

Refernces

• 1、 -. "NOVEL 1,3-DIHYDRO-BENZOIMIDAZOL-2-ONES AS M1 AGONISTS". Page/Page column 34. . Retrieved 2009/11/29.
• 2、 Burgey, Christopher S.,Stump, Craig A.,Nguyen, Diem N.,Deng, James Z.,Quigley, Amy G.,Norton, Beth R.,Bell, Ian M.,Mosser, Scott D.,Salvatore, Christopher A.,Rutledge, Ruth Z.,Kane, Stefanie A.,Koblan, Kenneth S.,Vacca, Joseph P.,Graham, Samuel L.,Williams, Theresa M.. "Benzodiazepine calcitonin gene-related peptide (CGRP) receptor antagonists: Optimization of the 4-substituted piperidine". . p. 5052 - 5056. Retrieved 2007/10/03.