66073-49-2

Basic information

• Product Name: 1-Azabicyclo[2.2.2]octane-2-carbonyl chloride, hydrochloride
• CAS NO: 66073-49-2
• Molecular Formula: C8H12ClNO.ClH
• Molecular Weight: 210.103
• Mol File: 66073-49-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-Azabicyclo[2.2.2]octane-2-carbonyl chloride, hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Azabicyclo[2.2.2]octane-2-carbonyl chloride, hydrochloride(66073-49-2)
• EPA Substance Registry System: 1-Azabicyclo[2.2.2]octane-2-carbonyl chloride, hydrochloride(66073-49-2)

Safety Data

• Hazardous Substances Data: 66073-49-2(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 112176-92-8 (+/-)-ethyl quinuclidine-2-carboxylate 
• 185223-21-6 (1-Aza-bicyclo[2.2.2]oct-2-yl)-[4-(3-trifluoromethyl-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 
• 72265-48-6 2-quinuclidinylbis(4-chlorophenyl)carbinol 
• 72265-55-5 2-quinuclidinyl(2-thiazolyl)(phenyl)carbinol 
• 72265-50-0 2-quinuclidinylbis(4-methylphenyl)carbinol 
• 72265-62-4 2-quinuclidinyl 4-chlorophenyl ketone 
• 72265-63-5 2-quinuclidinyl 4-methylphenyl ketone 
• 72265-47-5 erythro-2-quinuclidinyl-4-chlorophenylcarbinol 
• 72265-49-7 erythro-2-quinuclidinyl-4-methylphenylcarbinol 

Relevant articles and documents

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.

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.