106516-54-5

Basic information

• Product Name: 5-CHLORO-3-[1-((IMIDAZOLIDIN-2-ONE-1-YL)-ETHYL)-1,2,5,6-TETRAHYDROPYRIDIN-4-YL]-1-(4-FLUOROPHENYL)-INDOLE
• Synonyms: 5-CHLORO-3-[1-((IMIDAZOLIDIN-2-ONE-1-YL)-ETHYL)-1,2,5,6-TETRAHYDROPYRIDIN-4-YL]-1-(4-FLUOROPHENYL)-INDOLE
• CAS NO: 106516-54-5
• Molecular Formula: C₂₄H₂₄ClFN₄O
• Molecular Weight: 438.92
• Mol File: 106516-54-5.mol

Chemical Properties

• Boiling Point: 609.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.36±0.1 g/cm3(Predicted)
• PKA: 14.46±0.20(Predicted)
• CAS DataBase Reference: 5-CHLORO-3-[1-((IMIDAZOLIDIN-2-ONE-1-YL)-ETHYL)-1,2,5,6-TETRAHYDROPYRIDIN-4-YL]-1-(4-FLUOROPHENYL)-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-3-[1-((IMIDAZOLIDIN-2-ONE-1-YL)-ETHYL)-1,2,5,6-TETRAHYDROPYRIDIN-4-YL]-1-(4-FLUOROPHENYL)-INDOLE(106516-54-5)
• EPA Substance Registry System: 5-CHLORO-3-[1-((IMIDAZOLIDIN-2-ONE-1-YL)-ETHYL)-1,2,5,6-TETRAHYDROPYRIDIN-4-YL]-1-(4-FLUOROPHENYL)-INDOLE(106516-54-5)

Safety Data

• Hazardous Substances Data: 106516-54-5(Hazardous Substances Data)

Upstream product

• 460-00-4 1-Bromo-4-fluorobenzene 
• 17422-32-1 5-chloro-1H-indole 
• 2387-20-4 1-(2-chloroethyl)imidazolidin-2-one 
• 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 
• 138900-22-8 1-(4-fluorophenyl)-5-chloroindole 
• 41979-39-9 4-piperidone hydrochloride 
• 106516-07-8 5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)indole 

Relevant articles and documents

Identification and synthesis of impurities formed during sertindole preparation

Sertindole (1), an atypical anti-psychotic drug is used for the treatment of schizophrenia. During the laboratory optimization and later during its bulk synthesis the formation of various impurities was observed. The impurities formed were monitored and t

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.

Process for the preparation of 5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)indole and method of manufacturing sertindole

A process of manufacturing sertindole comprising reacting 5-chloro-1-(4-fluorophenyl)indole with 4-piperidone in a mixture of an acetic acid and concentrated HCl; reduction of the resulting 5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)indole and reaction of this compound with 1-(2-chloroethyl)-2-imidazolidinon in order to obtain sertindole.

Treatment of addiction to drugs and substances of abuse

1-Aryl-3-(4-1piperidyl)-indole derivatives having general formula (I), STR1 wherein R 1 is hydrogen, halogen, alkyl, alkoxy, hydroxy, cyano, nitro, alkylthio, trifluoromethyl, trifluoromethylthio, alkylsulfonyl, amino, alkylamino or dialkylaminio; R is op

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.