Acaprazine

Acaprazine (INN) is an anxiolytic and "adrenolytic" drug of the phenylpiperazine group that was never marketed.[1]

Acaprazine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
IUPAC name
  • N-[3-[4-(2,5-Dichlorophenyl)piperazin-1-yl]propyl]acetamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H21Cl2N3O
Molar mass330.25 g·mol−1
3D model (JSmol)
SMILES
  • CC(=O)NCCCN1CCN(CC1)C2=C(C=CC(=C2)Cl)Cl
InChI
  • InChI=1S/C15H21Cl2N3O/c1-12(21)18-5-2-6-19-7-9-20(10-8-19)15-11-13(16)3-4-14(15)17/h3-4,11H,2,5-10H2,1H3,(H,18,21) Y
  • Key:SGYVNBUUTWSSJC-UHFFFAOYSA-N Y
  (verify)

Synthesis
Patent:[2]

The Michael addition of acrylonitrile to 1-(2,5-Dichlorophenyl)Piperazine [1013-27-0] (1) gives the corresponding propionitrile (2).

Ex 1: Catalytic reduction over Raney nickel is performed in the presence of anhydrous sodium sulfate and acetic anhydride. This is a one-pot procedure for reducing the nitrile and mono acetylation of the primary amine produced in situ.

See also

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 488. ISBN 978-1-4757-2085-3.
  2. Giuseppe Palazzo, Bruno Silvestrini, DE 2432030 (1975 to Acraf).
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