Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of Spiro [4-hydroxycyclohexane-1, 4'-2', 3'-dihydro-6'-methoxy-2'-methyl-1'H-isoquinoline] and 4-Dimethylaminomethyl-4-(m-methoxyphenyl) cyclohexanol
TAMOTSU YASHIROKYOKO YAMADAHIDEAKI SHIRAI
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1975 Volume 23 Issue 9 Pages 2054-2057

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Abstract
For the purpose of testing the biological activity, spiro-[4-hydroxycyclohexane-1, 4'-2', 3'-dihydro-6'-methoxy-2'-methyl-1'H-isoquinoline] (IV) was synthesized by cyclization of 1-(m-methoxyphenyl)-4-hydroxycyclohexanemethylamine (XIII), which was obtained from the trans-acetoxy-amide (XII), in the presence of excess formic acid and formaldehyde under the conditions of Eschweiler-Clarke reaction. 4-Dimethylaminomethyl-4-(m-methoxyphenyl) cyclohexanol (V) was synthesized by reduction of 1-(m-methoxyphenyl)-4-acetoxycyclohexanecarbonyl dimethylamide (XIV), which was obtained from the trans-acetoxy-acid chloride (XI), with lithium aluminum hydride.
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© The Pharmaceutical Society of Japan
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