A novel spasmolytic and CNS active agent 3-(2-benzylmethylamino ethyl) benzoic acid methyl ester hydrochloride

1974 ◽  
Vol 30 (3) ◽  
pp. 271-272 ◽  
Author(s):  
N. R. Hansl
Xenobiotica ◽  
1987 ◽  
Vol 17 (12) ◽  
pp. 1405-1414 ◽  
Author(s):  
F.-J. Leinweber ◽  
A. J. Szuna ◽  
A. C. Loh ◽  
T. H. Williams ◽  
G. J. Sasso ◽  
...  

1983 ◽  
Vol 32 (6) ◽  
pp. 1093-1096 ◽  
Author(s):  
Maria Bianchi ◽  
Renzo Deana ◽  
Giuseppe Quadro ◽  
Gilles Mourier ◽  
Lauro Galzigna

1978 ◽  
Vol 33 (7-8) ◽  
pp. 465-471
Author(s):  
Franz Daliacker ◽  
Volker Mues ◽  
In-O Kim

Abstract We describe the possibilities of formation and preparation of the “natural” 1,3-benzodioxolecarboxylic acids 1, 2, 4, 6 b, and 7, already mentioned in literature. Myristic acid (3e) was prepared in good yield from 3-methoxy-4,5-dihydroxy-benzoic acid ester (3c) , which could be easily made from 3-methoxy-2,3-carbonyldioxy-benzoic acid methylester (3b). Myristicic acid methylester (3d) could be subjected to methylation and hydrolysis leading to 3e without any difficulties. 4.6-dimethoxy-1,3-benzodioxole-5-carboxylic acid (5b) was prepared in good yields by oxidation of 4,6-dimethoxy-1,3-benzodioxole-5-aldehyde (5a). 5.7-dimethoxy-1,3-benzodioxole-carboxylic acid (13f), one of the “unnatural” 1,3-benzodioxolecarboxylic acids, derivatives of o-ipiperonylic acid (8), was prepared from 5-amino-7-methoxy-1,3- benzodioxole-4carboxylic acid methyl ester (13b) by diazotisation, elimination of nitrogen, methylation, and hydrolysis. A comparison of our measured pkA-values showed the strongest acidity belonging to 5,6-dimethoxy-1,3-benzodioxole-4-carbocylic acid (11).


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