Quinuclidine hydrochloride

The 3-chloromelhyl-quinuclidine hydrochloride used as starling material in this process can be obtained as described by Grob and coll., Helv. Chim. Acta, 37 (1954), 1689. 

A freshly prepared 100-mL solution of Li [GaH4]16 (12.40 mmol) in diethyl ether is added by cannula to a 250-mL Schlenk flask containing a slurry of 2.15 g of quinuclidine hydrochloride in diethyl ether (50 mL) at 0°C. After gas evolution has ceased, the mixture is allowed to warm to ambient temperature and stirred for 16 h. The ethereal solution is decanted by filter-tipped cannula into a 250-mL Schlenk flask, concentrated to half volume in vacuo and cooled to ca. — 30°C for 16 h. Colorless crystals form. The supernatant liquid is decanted by cannula into another Schlenk flask and concentrated and cooled as above to give a second crop of crystals. Yield 2.06 g (90%). 

The first research on the pharmacological action of unsubstituted quinuclidines was made by Stern in 1941.178 In experiments on animals he established that quinuclidine hydrochloride causes a noticeable hypotensive activity and decreases the tone of smooth muscle. The corresponding quaternary salts display curarelike action. 

A solution of 0.6 g (0.006 mmol) of quinuclidine hydrochloride in 1 mL of water is neutralized with sodium hydroxide and ihen added to a solution of 1 g of Os04 in 25 mL of water. The solution is stirred for 5 min, the product filtered off, washed with water, and dried in vacuo. Recrystallization from CC14 gives bright red platelets mp 130 — 132"C. 

L-Tyrosine hydrochloride L-Cysteine methyl ester hydrochloride Quinuclidine hydrochloride p-Dichlorobenzene... 

However, V(N-C) values are observed for 1-propylamine, quinuclidine and their hydrochlorides. (94) In saturated amines it is unlikely that it will be possible to describe calculated 3/(N-C) values in terms of simple Karplus-type equations. Other factors, such as the orientation of the nitrogen lone-pair (important for 3/(N-H)), will undoubtedly be important. (124)... 

Azabicyclo(2.2.2)octan-3-one, hydrochloride EINECS 214-776-5 NSC 91498 Quinuclidin-3-one hydro-chloride 3-Quinuclidinone hydrochloride. Janssen Chimica Lancaster Synthesis Co. 

The carbon-carbon double bond in dehydrophenylalanine methyl ester, its hydrochloride salt, and its A -acetyl derivative has been hydrogenated enantioselectively over cinchonine-modified Pd giving a low excess of the S -enantiomer. In each case, a H-bonding interaction of the type -N- -H -N- is proposed between the amine function of the reactant and the quinuclidine-N of the modifier. On this basis, the mechanism is suggested to be analogous to that published for the hydrogenation of ap-unsaturated acids. 

In contrast to aceclidine in which introduction of a methyl radical in position 6 of the quinuclidine ring [compound (LVI)] led to a sharp reduction in activity, introduction of the same radical in the same position of the oxylidine molecule had not appreciable effect on the activity. The hydrochloride of 6-methyl-3-benzoyloxyquinuclidine [compound LXIV)] did not differ significantly from oxylidine in its hypotensive, adrenolytic, anticholinergic or sedative activities. 

Laboratory Chibret (France, West Germany) manufactures the hydrochloride of 3-acetoxy quinuclidine for the treatment of glaucoma under the trade name Glaucostat . 

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