66073-49-2

Upstream product

• 52601-23-7 quinuiclidine-2-carboxylic acid hydrochloride 

Downstream Products

• 185223-18-1 (1-Aza-bicyclo[2.2.2]oct-2-yl)-(4-p-tolyl-piperazin-1-yl)-methanone 
• 185223-23-8 (1-Aza-bicyclo[2.2.2]oct-2-yl)-[4-(4-methoxy-phenyl)-piperazin-1-yl]-methanone 
• 185223-24-9 (1-Aza-bicyclo[2.2.2]oct-2-yl)-[4-(2-chloro-phenyl)-piperazin-1-yl]-methanone 
• 185223-21-6 (1-Aza-bicyclo[2.2.2]oct-2-yl)-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone 
• 185223-25-0 (1-Aza-bicyclo[2.2.2]oct-2-yl)-[4-(3-chloro-phenyl)-piperazin-1-yl]-methanone 
• 185223-26-1 (1-Aza-bicyclo[2.2.2]oct-2-yl)-[4-(4-chloro-phenyl)-piperazin-1-yl]-methanone 
• 72265-54-4 (S)-(1-Aza-bicyclo[2.2.2]oct-2-yl)-(5-bromo-2-methoxy-phenyl)-(4-methoxy-phenyl)-methanol 
• 68483-88-5 erythro-phenyl-2-quinuclidinylcarbinol 
• 68483-88-5 threo-phenyl-2-quinuclidinylcarbinol 
• 72265-53-3 2-quinuclidinylbis(2-methoxy-5-bromophenyl)carbinol 
• 72265-52-2 2-quinuclidinylbis(4-methoxyphenyl)carbinol 

Relevant academic research and scientific papers

Synthesis of acyclic and heterocyclic derivatives of 2-carboxyquinuclidine. Part VIII

The 2-chlorocarbonylquinuclidine hydrochloride obtained from 2-carboxyquinuclidine hydrochloride was heated in benzene, in the presence of triethylamine, with the amines to give suitable piperazin-quinuclidinylcarboxyamides [I-X]. Some of the carboxyamides were reduced using LiAlH4 in diethyl ether and THF to the adequate piperazin-quinuclidinylmethylamines [XI-XV]. The structure of compounds obtained was confirmed by elementary analysis and IR spectra.

SYNTHESIS OF ACYCLIC AND HETEROCYCLIC DERIVATIVES OF 2-CARBOXYQUINUCLIDINE. VII.

The 2-chlorocarbonylquinuclidine hydrochloride received from 2-carboxyquinuclidine hydrochloride was heated in benzene, in the presence of triethylamine, with the amines to give suitable quinuclidinylcarboxyamides .Some of the carboxyamides were reduced using LiAlH4 in diethyl ether and THF to the adequate quinuclidinylmethylamines .The structure of compounds obtained was confirmed by elementary analysis and IR spectra.Keywords: derivatives of 2-carboxyquinuclidine, synthesis, elementary analysis, IR spectrum.

Mono- and diaryl-2-quinuclidinylcarbinols with local anesthetic and antiarrhythmic activity

The reaction between 2-carboethoxyquinuclidine and various aryl- and heteroaryllithium reagents gave mixtures of aryl 2-quinuclidinyl ketones and diaryl-2-quinuclidinylcarbinols. Diborane reduction of the ketones gave the erythro-carbinols, stereochemically analogous to quinidine. Several of the mono- and diarylcarbinols exhibited potent local anesthetic and antiarrhythmic activity, in some cases greater than that of quinidine. Diphenyl-2-quinuclidinylcarbinol and a (bromomethoxyphenyl)(methoxyphenyl)-2-quinuclidinylcarbinol were particularly active in reverting ouabain-induced arrhythmia in dogs, showing a potency and duration of action equal to or greater than that of propranolol.