Azaloxan

Azaloxan (CGS-7135A) is a drug which was patented as an antidepressant by Ciba-Geigy in the early 1980s, but was never marketed.[1]

Azaloxan
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 1-(1-{2-[(2S)-2,3-dihydro-1,4-benzodioxin-2-yl]ethyl}piperidin-4-yl)imidazolidin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H25N3O3
Molar mass331.416 g·mol−1
3D model (JSmol)
SMILES
  • O=C1NCCN1C2CCN(CC2)CC[C@@H]3Oc4c(OC3)cccc4
InChI
  • InChI=1S/C18H25N3O3/c22-18-19-8-12-21(18)14-5-9-20(10-6-14)11-7-15-13-23-16-3-1-2-4-17(16)24-15/h1-4,14-15H,5-13H2,(H,19,22)/t15-/m0/s1 Y
  • Key:CDFTVVPIMLXJRX-HNNXBMFYSA-N Y
 NY (what is this?)  (verify)

Synthesis

Thymoleptic described as a “psychostimulant” according to patent title.

Patent:[2]

The halogenation of allyl cyanide [109-75-1] (1) with bromine gives 3,4-dibromobutyronitrile [25109-74-4] (2). This is further reacted with catechol [120-80-9] (3) to give the 1,4-benzodioxan-2-yl-acetonitrile [18505-91-4] (4). Acid catalyzed hydrolysis of the nitrile to the acid gives 1,4-benzodioxan-2-yl-acetic acid [18505-92-5] (5). The reduction of this to alcohol with sodium bis(2-methoxyethoxy)aluminium hydride gives 2-(1,4-benzodioxan-2-yl)ethanol [62590-71-0] (6). The tosylation of this intermediate gives CID:12850582 (7). The synthesis concludes with an SN-2 displacement reaction with 1-(4-piperidinyl)-2-imidazolidinone [52210-86-3] (8) completing the synthesis of Azaloxan (9).

See also

References
  1. Triggle DJ (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.
  2. Charles F. Huebner, U.S. Patent 4,329,348 (1982 to Ciba-Geigy Corporation).


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