Spirodecanone

Chemical compound From Wikipedia, the free encyclopedia

Spirodecanone refers to a class of spirocyclic ketones, often studied for their potential applications in medicinal chemistry. One notable example is 1-Phenyl-1,3,8-triazaspiro[4.5]decan-4-one, which has been investigated as a metabolite of neuroleptic agents like Fluspirilene. It has a molecular formula of C13H17N3O and a melting point of 188-191 °C.

Quick facts Names, Identifiers ...
Spirodecanone
Names
Other names
1-Phenyl-1,3,8-triazaspiro[4,5]decan-4-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 213-819-5
MeSH spirodecanone
  • InChI=1S/C13H17N3O/c17-12-13(6-8-14-9-7-13)16(10-15-12)11-4-2-1-3-5-11/h1-5,14H,6-10H2,(H,15,17)
    Key: HTQWGIHCFPWKAS-UHFFFAOYSA-N
  • C1CNCCC12C(=O)NCN2C3=CC=CC=C3
Properties
C13H17N3O
Molar mass 231.299 g·mol−1
Density g/cm3 (20 °C)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis

The original synthesis was first disclosed by Paul Janssen,[1] and was covered by Daniel Lednicer in one of his books.[2]

A recent synthesis of spirodecanone is disclosed:[3][4]

The Strecker-like condensation between N-benzyl-4-piperidone [3612-20-2] (1), aniline and TMSCN [7677-24-9], gives 4-anilino-1-benzylpiperidine-4-carbonitrile [968-86-5] (2). Acid catalyzed partial hydrolysis of the nitrile to the amide afforded 4-anilino-1-benzylpiperidine-4-carboxamide [1096-03-3] (3). Reaction with DMF-DMA [de] forms the spiroimidazolidone ring giving 8-benzyl-1-phenyl-1,3,8-triazaspiro[4.5]dec-2-en-4-one [974-42-5] (4). The imine bond is reduced with sodium borohydride giving 8-benzyl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one [974-41-4] (5). Catalytic hydrogenation then removes the benzyl group (6).

It is noteworthy to mention that intermediate 4 finds dual use in the synthesis of some highly potent fentanyl analogs.[5]

Applications

Listed in alphabetical order:

  1. DiPOA
  2. Fluspiperone is similar but with additional para-fluoro.
  3. Fluspirilene
  4. L008716
  5. Phencyclidine analog[6]
  6. R-5260 [1109-69-9] (normethadone analog)
  7. R 6890 (spirochlorphine)
  8. RP-23618 [207991-30-8]
  9. Spiramide
  10. Spiroxatrine contains a Benzodioxan sidechain.
  11. Spirilene [357-66-4]
  12. Spiperone
  13. Ro64-6198 & Ro65-6570 (NOP receptor agonist).
  14. BRN 4620880 [99756-32-8]
  15. 8-(5,8-Dichloro-1,2,3,4-tetrahydro-2-naphthyl)-1-phenyl-1,3,8-triaza-spiro(4.5)decan-4-one.[7]

References

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