79617-95-1

Usage

Uses

Used in Pharmaceutical Industry:
4-(3,4-Dichlorophenyl)-1,2,3,4-Tetrahydrois used as an antidepressant for the treatment of depression and other mood disorders. It functions by inhibiting the reuptake of serotonin, a neurotransmitter that plays a crucial role in regulating mood, thereby increasing its availability in the synaptic cleft and enhancing its signaling.
Used in Research Applications:
4-(3,4-Dichlorophenyl)-1,2,3,4-Tetrahydrois also used as a research tool in the study of serotonin receptors and their role in various physiological and pathological processes. Its potent and selective inhibition of serotonin uptake makes it a valuable compound for investigating the mechanisms of action and potential therapeutic applications of SSRIs.
Used in Drug Development:
4-(3,4-Dichlorophenyl)-1,2,3,4-Tetrahydromay be utilized in the development of new drugs targeting serotonin receptors for the treatment of various conditions, including depression, anxiety, and other mood disorders. Its chemical properties and inhibitory effects on serotonin uptake make it a promising candidate for further research and development in the pharmaceutical industry.

Upstream product

• 15542-31-1 (2E,4E)-5-(3,4-Dichloro-phenyl)-penta-2,4-dienoic acid 
• 79560-20-6 N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine 
• 79560-19-3 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one 
• 74-89-5 methylamine 
• 18282-59-2 4-bromo-1,2-dichlorobenzene 
• 71-43-2 benzene 
• 151169-75-4 3,4-dichlophenylboronic acid 
• 90-15-3 α-naphthol 
• 95-50-1 1,2-dichloro-benzene 
• 79617-89-3 cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine hydrochloride 
• 79560-16-0 3-(ethoxycarbonyl)-4-(3,4-dichlorophenyl)-4-phenylbut-3-enoic acid 
• 79560-17-1 4-(3,4-dichlorophenyl)-4-phenylbut-3-enoic acid 
• 6284-79-3 3,4-dichlorobenzophenone 

Downstream Products

• 79617-98-4 (1R,4R)-sertraline 
• 79617-96-2 Sertraline 
• 244223-89-0 (cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate 

Relevant academic research and scientific papers

Sertraline racemate and enantiomer: Solid-state characterization, binary phase diagram, and crystal structures

The racemate and enantiomer of sertraline free base were prepared and characterized. The crystalline sertraline enantiomer is relatively less polymorphic compared with the sertraline-HCl salt. The solid-state nature of sertraline racemate was identified to be a racemic compound through a binary melting point phase diagram and spectroscopy analysis. The crystal structures of the racemate and enantiomer were determined to be monoclinic P121/n1 and P21, respectively.

Deactivation mechanisms of iodo-iridium catalysts in chiral amine racemization

The homogenous, [IrCp?I2]2, SCRAM catalyst (1) is active in the racemization of chiral amines. NMR, kinetic and structural mechanistic studies have determined the cause of catalyst deactivation to occur when ammonia or methylamine are liberated by hydrolysis or aminolysis of the intermediate imine, which tightly coordinate to the iridium centre to block turnover. Control of moisture and substrate concentration can suppress deactivation, whilst partial reactivation of spent catalyst was identified using hydroiodic acid.

Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents

A protocol for palladium-catalyzed dearomative functionalization of simple, nonactivated arenes with Grignard reagents has been established. This one-pot method features a visible-light-mediated [4+2] cycloaddition between an arene and an arenophile, and subsequent palladium-catalyzed allylic substitution of the resulting cycloadduct with a Grignard reagent. A variety of arenes and Grignard reagents can participate in this process, forming carboaminated products with exclusive syn-1,4-selectivity. Moreover, the dearomatized products are amenable to further elaborations, providing functionalized alicyclic motifs and pharmacophores. For example, naphthalene was converted into sertraline, one of the most prescribed antidepressants, in only four operations. Finally, this process could also be conducted in an enantioselective fashion, as demonstrated with the desymmetrization of naphthalene.

Intermolecular Radical C(sp3)?H Amination under Iodine Catalysis

The direct amination of aliphatic C?H bonds has remained one of the most tantalizing transformations in organic chemistry. Herein, we report on a unique catalyst system, which enables the elusive intermolecular C(sp3)?H amination. This practical synthetic strategy provides access to aminated building blocks and fosters innovative multiple C?H amination within a new approach to aminated heterocycles. The synthetic utility is demonstrated by the synthesis of four relevant pharmaceuticals.

MANGANESE (III) CATALYZED C--H AMINATIONS

Reactions that directly install nitrogen into C—H bonds of complex molecules are significant because of their potential to change the chemical and biological properties of a given compound. Selective intramolecular C—H amination reactions that achieve high levels of reactivity, while maintaining excellent site-selectivity and functional-group tolerance is a challenging problem. Herein is reported a manganese perchlorophthalocyanine catalyst [MnIII(ClPc)] for intermolecular benzylic C—H amination of bioactive molecules and natural products that proceeds with unprecedented levels of reactivity and site-selectivity. In the presence of Br?nsted or Lewis acid, the [MnIII(ClPc)]-catalyzed C—H amination demonstrates unique tolerance for tertiary amine, pyridine and benzimidazole functionalities. Mechanistic studies indicate that C—H amination proceeds through an electrophilic metallonitrene intermediate via a stepwise pathway where C—H cleavage is the rate-determining step of the reaction. Collectively these mechanistic features contrast previous base-metal catalyzed C—H aminations.

PROCESSES FOR THE PREPARATION OF SERTRALINE HYDROCHLORIDE

The invention relates to processes for the preparation of Schiff's base, and to the use of Schiff's base as intermediate in the preparation of naphthalenamine derivatives which are active compounds for treating the anxiety related disorders. The invention also relates to processes for the preparation of sertraline or a pharmaceutically acceptable salt thereof, and pharmaceutical compositions that include the sertraline.

Synthesis of dihydronaphthalenes via aryne Diels-Alder reactions: Scope and diastereoselectivity

Novel aryne Diels-Alder reactions with functionalized acyclic dienes are reported. These give useful cis-substituted dihydronaphthalene building blocks in good yield which are not easily accessible via other means, as demonstrated in the synthesis of sert

A new and simplified process for preparing N-[4-(3,4-dichlorophenyl)-3,4- dihydro-1(2H)-naphthalenylidene]methanamine and a telescoped process for the synthesis of (1S-cis)-4-(3,4-dichlorophenol)-1,2,3,4-tetrahydro-N-methyl-1- naphthalenamine mandelate: Key intermediates in the synthesis of sertraline hydrochloride

N-[4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]-methanamine, sertraline imine (3), is an intermediate for the synthesis of Zoloft, sertraline hydrochloride (1). A cleaner, simpler, and more efficient alternative to the Schiff base-mediated formation of sertraline imine has been developed and is presented in this paper. The condensation reaction between 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalone, sertraline tetralone (2), and monomethylamine was carried out in ethanol, without the need for classical dehydrating agent, such as TiCl4, or more novel approaches, such as molecular sieves, both of which produce hazardous byproducts and solid wastes. The low solubility of the imine 3 in this type of solvent is exploited, such that the reaction equilibrium favorably enhances the imine formation. Furthermore, an improved and highly selective catalytic reduction of 3 with Pd/CaCO3 catalyst in ethanol as the reaction solvent, followed by the resolution of the racemic cis isomer (6) with D-(-)-mandelic acid results in a more efficient telescoped commercial process to (1S-cis)-4-(3,4-dichlorophenol)- 1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine mandelate, sertraline mandelate (4). This new process has been implemented commercially and eliminates the use of hazardous material such as TiCl4, significantly reduces undesirable byproducts, reduces the number of intermediate isolations, and improves the overall process yield and productivity on industrial scale.

IMPROVED SYNTHESIS OF RACEMIC SERTRALINE

The present invention relates to the use or natural vegetable flavouring components as flavouring agents in chewing gum coating. The addition of a natural vegetable component to a chewing gum coating results in increased flavour sensation. The invention also relates to a method for the preparation of a chewing gum wherein the coating comprises a natural vegetable component as flavouring agent. The chewing gum comprises a) an insoluble gum base; b) a water soluble portion; c) a coating comprising a flavouring agent wherein at least 10% by weight of the flavouring agent is a natural vegetable flavouring agent comprising plant cellular material.

The preparation and intra- and intermolecular addition reactions of acyclic N-acylimines: Application to the synthesis of (±)-sertraline

Intramolecular endo-cyclization reactions of N-acyliminium ions have seen wide application for the synthesis of heterocyclic compounds. The corresponding exocyclic variant, which would provide 1-aminotetralin derivatives, for example, has little precedent. We have discovered that acyclic N-acylcarbamates can be readily reduced to the corresponding N-acylhemiaminal derivatives in high yield using DIBAL as the reducing agent. These intermediates are remarkably stable and, if desired, can be purified and stored. The acyclic N-acylhemiaminals undergo both intra- and intermolecular nucleophilic addition reactions mediated by strong Lewis acids, such as TiCl4. Diastereoselectivity, induced either by a substituent on the newly formed ring, or by utilizing a chiral ester on the carbamic acid, was disappointingly low. This methodology was successfully applied to the synthesis of the racemic form of the marketed antidepressant sertraline.