An Alternative Synthesis of So-called Corpaverine (Studies on the Syntheses of Heterocyclic Compounds. CCXXXI)
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概要
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Brossi and Teitel have recently reported a synthesis of so-called corpaverine (I), mp 115-117°, whose IR and NMR spectra were identical with those of our sample, but the melting points of both specimens were not identical. Therefore, we have re-examined the synthesis of so-called corpaverine. Cyclization of N-(3-benzyloxy-4,5-dimethoxy-phenethyl)-4-methoxyphenylacetamide with phosphoryl chloride afforded two isomers, one of which was isolated as its crystals, mp 84-86°, identical with our sample (I) reported previously. Furthermore, the synthesis of 7,8-dimethoxy-1-(4-methoxybenzyl)-2-methyl-3,4-dihydroisoquinolin-6-ol (IV) by Grignard reaction was carried out in order to compare our sample with Brossi's sample. At first the cyclization of the formyl derivative (VI) with phosphoryl chloride afforded a mixture of VII and VIII, which was separated by recrystallization of its perchlorates. After reduction with sodium borohydride, 8-benzyloxy-derivative (IX) was obtained as its hydrochloride, mp 188-190°, whose debenzylation gave the anhalamine hydrochloride. Secondly Grignard reaction of the methobromide (XIII) with 4-methoxybenzylmagnesium chloride afforded the benzyl-derivative (XV), whose debenzylation with acid gave a phenolic base, mp 84-86°. The IR (in CHCl_3) and NMR (in CDCl_3) spectra of this sample were not only identical with those of our authentic sample reported by us previously, but also with those of Brossi's sample, mp 115-117°. Accordingly we have concluded to confirm the identity between both specimens and suggesting polymorphism.
- 社団法人日本薬学会の論文
- 1968-05-25
著者
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亀谷 哲治
Pharmaceutical Institute, Tohoku University School of Medicine
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大久保 一三
Pharmaceutical Institute, Tohoku University School of Medicine
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大久保 一三
グレラン製薬研究開発部
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亀谷 哲治
Pharmaceutical Institute Medical Faculty University Of Osaka
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亀谷 哲治
Toyama Technical College
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