149620-65-5

Upstream product

• 79560-18-2 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid 
• 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

• 79836-45-6 trans-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine 
• 79617-96-2 Sertraline 
• 79951-46-5 trans-(1R,4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine 
• 91797-60-3 trans-(1S,4R)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine 
• 79617-98-4 (1R,4R)-sertraline 
• 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 
• 848130-45-0 [4-(3,4-dichlorophenyl)-4-phenylbutyryl]carbamic acid methyl ester 
• 79617-95-1 cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine 

Relevant academic research and scientific papers

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.

Nontricyclic Antidepressant Agents Derived from cis- and trans-1-Amino-4-aryltetralins

The need for drugs that lack the obtrusive and limiting side effects of the tricyclic antidepressants has prompted the search for agents with greatly enhanced selectivity for specific mechanisms believed to be essential for antidepressant efficacy.The potential role of derangements of 5-HT pathways in the etiology of depression has long been suspected and has given impetus to the development of newer compounds that accentuate inhibition of serotonin reuptake.This paper presents structure-activity relationship for a series of cis-1-amino-4-(substituted-aryl)tetralins, which are surprisingly potent and selective inhibitors of serotonin uptake in in vitro models.These compounds are pharmacologically distinct from corresponding members of the trans series, which also potently block uptake of dopamine and norepinephrine.The activity in both cis and trans series is stereospecific, being restricted to the cis-(1S,4S) and the trans-(1R,4S) enantiomers.