106516-07-8

Basic information

• Product Name: 5-CHLORO-1-(4-FLUORO-PHENYL)-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE
• Synonyms: 5-Chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole;5-CHLORO-1-(4-FLUORO-PHENYL)-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE
• CAS NO: 106516-07-8
• Molecular Formula: C₁₉H₁₆ClFN₂
• Molecular Weight: 326.7951432
• Mol File: 106516-07-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 481℃
• Flash Point: 245℃
• Appearance: /
• Density: 1.29
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-CHLORO-1-(4-FLUORO-PHENYL)-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-1-(4-FLUORO-PHENYL)-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE(106516-07-8)
• EPA Substance Registry System: 5-CHLORO-1-(4-FLUORO-PHENYL)-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE(106516-07-8)

Safety Data

• Hazardous Substances Data: 106516-07-8(Hazardous Substances Data)

Usage

General Description

5-CHLORO-1-(4-FLUORO-PHENYL)-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is a chemical compound with a complex structure. It contains a chlorine atom, a 4-fluoro-phenyl group, and a 1,2,3,6-tetrahydro-pyridin-4-yl group, all attached to a 1H-indole ring. 5-CHLORO-1-(4-FLUORO-PHENYL)-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE may have potential applications in medicinal chemistry, as the indole ring is a common structural motif in many biologically active compounds. The presence of the fluorine and chlorine atoms could also impart specific chemical and pharmacological properties to the molecule, making it of interest for further research and development in drug discovery.

Upstream product

• 40064-34-4 piperidine-4,4-diol hydrochloride 
• 138900-22-8 1-(4-fluorophenyl)-5-chloroindole 
• 138900-12-6 methyl 5-chloro-1-(4-fluorophenyl)-3-hydroxy-1H-indol-2-carboxylate 
• 948553-95-5 5-Chloro-1-(4-fluoro-phenyl)-2,3-dihydro-1H-indol-3-ol 
• 170232-17-4 5-chloro-2,3-dihydro-1-(4-fluorophenyl)-1H-indol-3-one 
• 41979-39-9 4-piperidone hydrochloride 

Downstream Products

• 106516-54-5 1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]-1,2,3,6-tetrahydro-1-pyridyl]ethyl]-2-imidazolidinone 
• 138900-50-2 1-(2-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-ethyl)-3-cyclopentyl-imidazolidin-2-one 
• 138900-48-8 1-(2-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-ethyl)-3-isopropyl-imidazolidin-2-one 
• 138900-44-4 1-(6-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-hexyl)-imidazolidin-2-one 
• 138900-42-2 1-(5-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-pentyl)-imidazolidin-2-one 
• 138900-40-0 1-(4-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-butyl)-imidazolidin-2-one 
• 138900-38-6 1-(3-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-propyl)-imidazolidin-2-one 
• 138900-46-6 1-(2-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-ethyl)-3-methyl-imidazolidin-2-one 
• 138900-52-4 1-(2-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-ethyl)-3-phenyl-imidazolidin-2-one 
• 106516-24-9 Sertindole 
• 138900-27-3 5-chloro-1-(4-fluorophenyl)-3-(4-piperidinyl)-1H-indole 

Relevant articles and documents

Method of manufacturing sertindole

The present invention relates to a new method of manufacturing the compound 1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1-H-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinone having the recommended INN name sertindole and a new method of manufacturing the intermediates, N-(4-fluorophenyl)-N-(2-carboxy-4-chlorophenyl)glycine and 5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)indole used in the method.

Noncataleptogenic, centrally acting dopamine D-2 and serotonin 5-HT2 antagonists within a series of 3-substituted 1-(4-fluorophenyl)-1H-indoles

A series of 1-(4-fluorophenyl)-1H-indoles substituted at the 3-position with 1-piperazinyl, 1,2,3,6-tetrahydro-4-pyridinyl, and 4-piperidinyl was synthesized. Within all three subseries potent dopamine D-2 and serotonin 5- HT2 receptor affinity was found in ligand binding studies. Quipazine-induced head twitches in rats were inhibited by most derivatives as a measure of central 5-HT2 receptor antagonism. Piperazinyl and tetrahydropyridyl indoles were cataleptogenic, while piperidyl substituted indoles surprisingly were found to be noncataleptogenic or only weakly cataleptogenic. Noncataleptogenic piperidyl derivatives also failed to block dopaminergic- mediated stereotypies, that is methyl phenidate-induced gnawing behavior in mice. These profiles resemble that of the atypical neuroleptic clozapine. 1- Ethyl-2-imidazolidinone was found to be the optimal substituent of the basic nitrogen atom in order to avoid catalepsy. The atypical neuroleptic 1-[2-[4- [5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]-1-piperidinyl]ethyl]-2- imidazolidinone (sertindole, compound 14c) was selected for further development as a result of these structure/activity studies.