Does anyone know anything about the precursors mentioned on
https://www.thevespiary.org/rhodium/Rhodium/chemistry/levorphanol.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/levorphanol.html)
for making levophanol/racemorphan?
Especially:
2-(1,4-Cyclohexadienyl)ethylamine
and
p-Methoxyphenylacetyl chloride
I cannot find any information on these, do they have any other names? Any info on synthesis of these would be greatly appreciated!
The first one is made though birch reduction of 2-phenetylamine, and the second through chlorination of 4-methoxyphenylacetic acid with SOCl
2. One synthesis of the latter precursor can be found at
https://www.thevespiary.org/rhodium/Rhodium/chemistry/willgerodt.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/willgerodt.html)
but there are others.
If you have the necessary equipment to perform the above reactions I'll help you further.
Preparation of useful intermediates of dextrorphan
Passarotti, C. M.; Valenti, M.; Grianti, M.
Boll.Chim.Farm. 1993, 132: 11 472-474
Dextrorphan is the main metabolite of Dextromethorphan, a drug with high anti-tussive activity.In this preliminary work we report on the synthesis of two essential intermediates for its preparation: 2-(1-cyclohexenyl)ethyl amine and (R;S)-1-(4-methoxy-benzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline.KEY-WORDS: Dextrorphan-intermediates; Alcohol-dehydration; LiAlH4-reduction; NaBH4-reduction; C-alkylation 2-(1-cyclohexenyl)ethylamine; 1,2,3,4,5,6,7,8-octahydroisoquinoline-derivatives; Nitrile reduction to primary amine
you can use 2-(1-cyclohexenyl)ethyl amine in place of the dihydro phenethylamine. i think this can be prepared from cyclohexanone starting with a grignard. the above ref is from the belstein databases - perhaps some kind bee with access to the complete article could post it or alternatively pm blondie.