Desmethylmoramide

Desmethylmoramide (INN) is an opioid analgesic related to dextromoramide (the active (+)-isomer of moramide) that was synthesized and characterized in the late 1950s but was never marketed.[1][2][3]

Desmethylmoramide
Names
Preferred IUPAC name
4-(Morpholin-4-yl)-2,2-diphenyl-1-(pyrrolidin-1-yl)butan-1-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C24H30N2O2/c27-23(26-14-7-8-15-26)24(21-9-3-1-4-10-21,22-11-5-2-6-12-22)13-16-25-17-19-28-20-18-25/h1-6,9-12H,7-8,13-20H2
    Key: JRPANCYSRUEJDY-UHFFFAOYSA-N
  • C1CCN(C1)C(=O)C(CCN2CCOCC2)(C3=CC=CC=C3)C4=CC=CC=C4
Properties
C24H30N2O2
Molar mass 378.516 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis
Patent:[4]

The starting diphenylacetylpyrrolidine [60678-46-8] can be made in ~84% yield by the reaction of methyldiphenylacetate with pyrrolidine.[5] Or ~62% from amidation of the free acid (by Schotten-Baumann reaction).[6]

See also

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 363–. ISBN 978-1-4757-2085-3.
  2. Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 94–. ISBN 978-94-011-4439-1.
  3. Janssen PA, Jageneau AH (June 1957). "A new series of potent analgesics: dextro 2:2-diphenyl-3-methyl-4-morpholino-butyrylpyrrolidine and related amides. I. Chemical structure and pharmacological activity". The Journal of Pharmacy and Pharmacology. 9 (6): 381–400. doi:10.1111/j.2042-7158.1957.tb12290.x. PMID 13439527. S2CID 58956931.
  4. Anon., GB 822055 (1959 to Nl Combinatie Chem Ind Lab Pharmaceutica Dr C Janssen).
  5. Dubois, N., Glynn, D., McInally, T., Rhodes, B., Woodward, S., Irvine, D. J., Dodds, C. (November 2013). "On DABAL-Me3 promoted formation of amides". Tetrahedron. 69 (46): 9890–9897. doi:10.1016/j.tet.2013.08.062. ISSN 0040-4020.
  6. Liepa, A. (1982). "A synthesis of alkylated 3-aminoisoquinolines and related compounds". Australian Journal of Chemistry. 35 (7): 1391. doi:10.1071/CH9821391. ISSN 0004-9425.

Further reading
  • Davis MA, Winthrop SO, Stewart J, Sunahara FA, Herr F (May 1963). "New Psychotropic Agents. V. Derivatives of 5-Cyano- and 5-Carboxamidodibenzo[a,d]cycloheptadiene". Journal of Medicinal Chemistry. 6 (3): 251–255. doi:10.1021/jm00339a008. PMID 14185978.
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