Diclofensine

Source: Wikipedia, the free encyclopedia.
Diclofensine
Clinical data
ATC code
  • None
Legal status
Legal status
  • In general: legal
Identifiers
  • 4-(3,4-dichlorophenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
JSmol)
  • CN1CC(C2=C(C1)C=C(C=C2)OC)C3=CC(=C(C=C3)Cl)Cl
  • InChI=1S/C17H17Cl2NO/c1-20-9-12-7-13(21-2)4-5-14(12)15(10-20)11-3-6-16(18)17(19)8-11/h3-8,15H,9-10H2,1-2H3 ☒N
  • Key:ZJDCGVDEEHWEIG-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Diclofensine (Ro 8-4650) was developed by

abuse potential.[12][13]

Diclofensine is chemically a tetrahydroisoquinoline (THIQ) derivative, as is nomifensine.

Synthesis

Patents:[14][15] Also:[16]

The condensation of m-anisaldehyde [591-31-1] (1) with methylamine gives N-methyl-3-methoxybenzenemethanimine [16928-30-6]. Reduction of this Schiff-base intermediate with sodium borohydride gives (3-methoxybenzyl)methylamine [41789-95-1] (2). Alkylation of this with 3,4-dichlorophenacylbromide [2632-10-2] (3) would give CID:59580342 (4). Reduction of the benzoyl ketone with sodium borohydride gives the alcohol [802051-24-7] (5). Acid catalyzed intramolecular cyclization then completes the synthesis of the 4-aryl-THIQ derivative, diclofensine (6).

See also

References

  1. ^ US Patent 3947456 A, Alfred Rheiner, "Substituted 4-Phenyl Isoquinolines", published 1976-03-30, assigned to Hoffman-La Roche Inc. 
  2. ISBN 978-0-8493-9140-8.{{cite book}}: CS1 maint: location (link
    )
  3. PMID 6979165
    .
  4. PMID 7107085
    .
  5. PMID 2968488
    .
  6. S2CID 34977195
    .
  7. PMID 2530094
    .
  8. S2CID 41618656
    .
  9. PMID 6379345
    .
  10. S2CID 36360683
    .
  11. PMID 6860528
    .
  12. S2CID 25043692
    .
  13. PMID 7589207
    .
  14. ^ Rheiner Alfred Jr Dr, CH 538477  (1973 to Hoffmann La Roche).
  15. ^ Alfred Rheiner, U.S. patent 3,947,456 (1976 to Hoffman-La Roche Inc.).
  16. ^ Shuang Liu, Bruce F. Molino, Kassoum Nacro, WO 2010132442  (2010 to Albany Molecular Reserch, Inc.). Page column 32.
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