Chemistry:Etifelmine

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Etifelmine (INN; also known as gilutensin) is a stimulant drug. It was used for the treatment of hypotension (low blood pressure).[1]

Synthesis

The base-catalyzed reaction between benzophenone (1) and butyronitrile (2) gives 2-[hydroxy(diphenyl)methyl]butanenitrile (3).[2][3] Catalytic hydrogenation reduces the nitrile group to a primary amine giving 1,1-diphenyl-2-ethyl-3-aminopropanol (4). The tertiary hydroxyl group is dehydrated by treatment with anhydrous hydrogen chloride gas, completing the synthesis of etifelmine (5).

Synthesis of etifelmine

See also

References

  1. "The treatment of hypotensive circulatory disorders with gilutensin." (in German). Therapie der Gegenwart 103: 1007–12. August 1964. PMID 14254672. 
  2. Etifelmine, Thieme
  3. Dr Werner Heinrich & Dr Walter Heigel, DE patent 1122514 (1962 to Giulini Gmbh Geb).