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Draft:Furomazine

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Furomazine
Identifiers
  • 3-[1-[3-(2-chlorophenothiazin-10-yl)propyl]-4-hydroxypiperidin-4-yl]oxolan-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC24H27ClN2O3S
Molar mass459.00 g·mol−1
3D model (JSmol)
  • C1COC(=O)C1C2(CCN(CC2)CCCN3C4=CC=CC=C4SC5=C3C=C(C=C5)Cl)O
  • InChI=InChI=1S/C24H27ClN2O3S/c25-17-6-7-22-20(16-17)27(19-4-1-2-5-21(19)31-22)12-3-11-26-13-9-24(29,10-14-26)18-8-15-30-23(18)28/h1-2,4-7,16,18,29H,3,8-15H2
  • Key:PRGQOVDEZVJQJK-UHFFFAOYSA-N

Furomazine is a phenothiazine sedative and neuroleptic agent.[1]

Synthesis

[edit]

A chemical synthesis is proposed:[2] The mesylate leaving group on the phenothiazine used in the patent is less common than a chloride. This is because it is more facile to displace and therefore avoids side-reactions with the lactone.

Furomazine synthesis
Furomazine synthesis
  • 1-benzyl-4-piperidone [3612-20-2] (1)
  • Gamma-Butyrolactone [96-48-0] (2)
  • alpha-(1-Benzyl-4-hydroxy-4-piperidyl)-gamma-butyrolactone [28532-91-4] (3)
  • 3-(4-hydroxypiperidin-4-yl)oxolan-2-one, PC129932729 (4)
  • 3-(2-chlorophenothiazin-10-yl)propyl methanesulfonate, PC154087390 (5)

References

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  1. ^ Dictionary of Pharmacological Agents By C.R. Ganellin, David J. Triggle.
  2. ^ ZA6802527 (1969) idem Anton Ebnother, Ernst Jucker, Erwin Rissi, US3531480 (1970 to Sandoz Ag).