Jump to content

Spirodecanone

From Wikipedia, the free encyclopedia
This is an old revision of this page, as edited by 92.31.192.97 (talk) at 07:41, 13 June 2025 (Synthesis). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.
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
  • 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 231.29 g/mol
Density g/cm3 (20°C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Synthesis

The original synthesis was first disclosed by Janssen,[1] and was covered by Daniel Lednicer and Lester Mitscher in one of their books.

A recent synthesis of spirodecanone is disclosed:[2][3]

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).

Applications

Listed in alphabetical order:

  1. Fluspiperone is similar but with additional para-fluoro.
  2. Fluspirilene
  3. L008716
  4. R 5260 [1109-69-9] (normethadone analog)
  5. R 6890 (spirochlorphine)
  6. RP-23618 [207991-30-8]
  7. Spiramide
  8. Spiroxatrine contains a Benzodioxan sidechain.
  9. Spirilene [357-66-4]
  10. Spiperone
  11. Ro64-6198 & Ro65-6570 (NOP receptor agonist).
  12. [99756-32-8]

References

  1. ^ Janssen Paul Adriaan Jan, US3155669, US3155670, US3161644 & US3238216 (1964, 1964, 1964 & 1966 all to Research Laboratorium C Janssen NV).
  2. ^ Morciano, G., Preti, D., Pedriali, G., Aquila, G., Missiroli, S., Fantinati, A., Caroccia, N., Pacifico, S., Bonora, M., Talarico, A., Morganti, C., Rizzo, P., Ferrari, R., Wieckowski, M. R., Campo, G., Giorgi, C., Trapella, C., Pinton, P. (23 August 2018). "Discovery of Novel 1,3,8-Triazaspiro[4.5]decane Derivatives That Target the c Subunit of F 1 /F O -Adenosine Triphosphate (ATP) Synthase for the Treatment of Reperfusion Damage in Myocardial Infarction". Journal of Medicinal Chemistry. 61 (16): 7131–7143. doi:10.1021/acs.jmedchem.8b00278.
  3. ^ 盛春泉, et al. CN113480536 (2021 to Second Military Medical University SMMU).