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 .5ecan-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

Paul Janssen Paul Adriaan Jan, Baron Janssen (12 September 1926 – 11 November 2003) was a Belgian physician. He was the founder of Janssen Pharmaceutica, a pharmaceutical company with over 20,000 employeesPaul Lewi, Obituary of Dr Paul Janssen (1926–20 ...

, and was covered by Daniel Lednicer in one of his books. A recent synthesis of spirodecanone is disclosed: Spirodecanone synthesis

The Strecker-like condensation between N-benzyl-4-piperidone 612-20-2(1),

aniline Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...

and TMSCN 677-24-9 gives 4-anilino-1-benzylpiperidine-4-carbonitrile 68-86-5(2). Acid catalyzed partial hydrolysis of the

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ...

to the

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...

afforded 4-anilino-1-benzylpiperidine-4-carboxamide 096-03-3(3). Reaction with forms the spiroimidazolidone ring giving 8-benzyl-1-phenyl-1,3,8-triazaspiro .5ec-2-en-4-one 74-42-5(4). The imine bond is reduced with

sodium borohydride Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula (sometimes written as ). It is a white crystalline solid, usually encountered as an aqueous basic solution. Sodi ...

giving 8-benzyl-1-phenyl-1,3,8-triaza-spiro .5ecan-4-one 74-41-4(5).

Catalytic hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic ...

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.

Applications

Listed in alphabetical order:
Fluspiperone
is similar but with additional para-fluoro. #

Fluspirilene Fluspirilene (Redeptin, Imap, R6218) is a diphenylbutylpiperidine typical antipsychotic drug, used for the treatment of schizophrenia. It is administered intramuscularly. It was discovered at Janssen Pharmaceutica in 1963. A 2007 systematic revi ...

L008716Phencyclidine analog
ref> # R 5260 109-69-9(normethadone analog) # R 6890 (

spirochlorphine R6890, sometimes known as spirochlorphine, is an opioid analgesic and a member of the spiropiperidine family of agents. The first known mention of this compound was in 1977. It has been advertised online as a research chemical having a potency 2 ...

)
RP-23618
07991-30-8#

Spiramide Spiramide (developmental code name AMI-193) is an experimental antipsychotic that acts as a selective 5-HT2A, 5-HT1A, and D2 receptor antagonist. It has negligible affinity for the 5-HT2C receptor. See also *Spirodecanone Spirodecanone ref ...

Spiroxatrine Spiroxatrine (Spiroxamide, R5188) is a drug which acts as a selective antagonist at both the 5-HT1A receptor and the α2C adrenergic receptor. It is an analog of spiperone and also has some dopamine antagonist effects and a relatively weak opio ...

contains a Benzodioxan sidechain.
Spirilene
57-66-4#

Spiperone Spiperone, also known as spiroperidol and sold under the brand name Spiropitan (( JP)) is a typical antipsychotic of the butyrophenone family related to haloperidol. It is approved for clinical use in Japan as a treatment for schizophrenia. Pha ...

Ro64-6198 Ro64-6198 is an opioid drug used in scientific research. It acts as a potent and selective agonist for the nociceptin receptor, also known as the ORL-1 (opiate receptor like-1) receptor, with over 100x selectivity over the other opioid receptors. ...

Ro65-6570 Ro65-6570 is an opioid drug. It has a potential use in preventing the addiction to other opioids. Mechanism of action Ro65-6570 is an opioid drug, it works by activating opioid receptors. However, instead of acting at the mu, kappa and delt ...

(NOP receptor agonist). #BRN 4620880 9756-32-8

References

{{reflist Belgian inventions Spiro compounds Imidazolidinones Piperidines Anilines