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Synthesis of papaverine and quinopavine specifically labeled with 14C

✍ Scribed by S. D. Ithakissios; G. Tsatsas; J. Nikokavouras; A. Tsolis

Publisher
John Wiley and Sons
Year
1974
Tongue
French
Weight
486 KB
Volume
10
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

1‐(3,4‐Dirmethoxybenzyl)‐6, 7‐dimethoxyisoquinoline (papaverine) labeled with ^14^C in either the benzyl or 4‐carbon position and 1‐(3,4‐dimethoxyphenyl) 6,7‐dimethoxyisoquinoline (quinopavine) labeled with ^14^C at the 1,4 or 4‐methoxyphenyl position were synthesized. The 3,4‐dimethoxybenzoic acid‐carboxyl‐^14^C.(I) was, employed as the precursor in the synthesis of, all the above compounds except the 4‐methoxyphenyl labeled where 3‐methoxy‐4‐^14^C‐methoxybenzoic acid was employed (XII). The reduction of 3,4‐dimethoxybenzoylchloride ^14^C (VII) led to the formation of 3,4‐dimethoxybenzaldehyde‐carbonyl ^14^‐C (VIII) from which 2‐(3,4‐dimethoxyphenyl)‐2‐methoxyethylamine‐2‐^14^C (XI) was obtained through reduction of the corresponding ^14^C‐labeled substituted nitrostyrene (IX). 3,4‐Dimethoxybenzoic acid‐carboxyl‐^14^C (I) was employed in the synthesis of (3,4‐dimethoxyphenyl)‐acetonitrile‐2‐^14^C (IV) from which a) 2‐(3,4‐dimethoxyphenyl)‐ethylamine‐2‐^14^C (VI) was obtained on reduction and b) (3,4‐dimethoxyphenyl)‐acetic acid‐2‐^14^C (V) on alkaline hydrolysis. On heating together at 200°C the corresponding acids and amines in the absence as well as in the presence of decaline (solvent), or by a Schotten‐Bawmann reaction, the corresponding amines were obtained and them cyclized in the presence of phosphorus oxychloride. The 3, 4‐dihydro‐products were dehydrogenated in the presence of palladium‐pumice which acted as a catalyst. The cyclization of N‐(3,4‐dimethoxyphenyl‐2‐methoxyethyl‐2‐^14^C) 3,4‐dimethoxyphenyl‐acetamide (XVI) gave straightway the corresponding ^14^C) 3,4‐dimethoxyphenyl‐acetamide (XVI) gave straightway the corresponding ^14^C‐marked papaverine.

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