Synthesis of N-benzoylhomomeroquinene (18.104.22.168) is carried out using 7-oxyisoquino-line (22.214.171.124), which is made by reacting of aminoacetal with m-hydroxybenzaldehyde with isolation of the intermediate imine (126.96.36.199), which then cyclizes in the presence of sulfuric acid to the starting substance—7-oxyisoquinoline (188.8.131.52). The resulting 7-oxy-isoquinoline is aminomethoxided with a mixture of formaldehyde and piperidine to make 7-oxy-8-piperidinomethylisoquinoline (184.108.40.206). Reducing this with hydrogen using a palladium catalyst removes the piperidine fragment, giving 7-oxy-8-methylisoquinoline
(220.127.116.11). This is again reduced with hydrogen in order to hydrogenate the pyridine fragment, except this time a palladium oxide catalyst is used. This forms 7-oxy-8-methylte-trahydroisoquinoline (18.104.22.168). N-Acylating the resulting compound with acetic anhydride and then hydrogenating it with hydrogen using a platinum catalyst gives a mixture of stereoisomeric N-acetyl-7-oxy-8-methyldecahydroisoquinolines, from which the cw-isomer (22.214.171.124) is isolated. It is oxidized using chromium(VI) oxide to N-acetyl-7-keto-8-methyldecahydroisoquinoline (126.96.36.199). Reacting this with ethyl nitrite in the presence of sodium ethoxide cleaves up the methylcyclohexanone fragment, giving N-acetyl-10-oxyminodihydrohomomeroquinene (188.8.131.52), which is then reduced in the presence of a platinum catalyst to the amine (184.108.40.206). This undergoes exhaustive methy-lation using methyl iodide to make a quaternary salt (220.127.116.11), which is then cleaved on heating in concentrated alkali, giving racemic homomeroquinene (18.104.22.168). Successive esterification and subsequent benzoylation of the product gives the ethyl ester of N-benzoylhomomeroquinene (22.214.171.124).
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