JoNn26 (Stranger)
06-10-02 01:33
No 319230
      Levorphanol precursors  Bookmark   

Does anyone know anything about the precursors mentioned on ../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!
 
 
 
 
    Rhodium
(Chief Bee)
06-10-02 02:37
No 319238
      Precursors  Bookmark   

The first one is made though birch reduction of 2-phenetylamine, and the second through chlorination of 4-methoxyphenylacetic acid with SOCl2. One synthesis of the latter precursor can be found at ../rhodium/chemistry /willgerodt.html but there are others.

If you have the necessary equipment to perform the above reactions I'll help you further.
 
 
 
 
    blondie
(Newbee)
06-10-02 10:24
No 319328
      TITLE Preparation of useful intermediates of ...  Bookmark   

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.