Names | |
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Preferred IUPAC name Piperidin-4-one | |
Other names 4-Piperidone Azinanone Azinan-4-one | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.050.420 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C5H9NO | |
Molar mass | 99.133 g·mol−1 |
Boiling point | 79 °C (174 °F; 352 K) |
Hazards | |
GHS labelling: | |
Warning | |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 91 °C (196 °F; 364 K) |
Related compounds | |
Related compounds | Piperidine; 2-Piperidinone |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
4-Piperidone is an organic compound with the molecular formula OC(CH2)4NH. It can be viewed as a derivative of piperidine. 4-Piperidone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs. Substituted and dehydro derivatives of 4-piperidinone are intermediates in alkaloid syntheses. [1]
The N-protonated derivative is typically isolated as the hydrate (HO)2C(CH2)4NH+2. [2]
It is a List I chemical in the United States as it is a precursor to fentanyl.
Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one methine group (=CH−) replaced by a nitrogen atom (=N−). It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide.
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, typical of amines. The name comes from the genus name Piper, which is the Latin word for pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins.
In organic chemistry, thioesters are organosulfur compounds with the molecular structure R−C(=O)−S−R’. They are analogous to carboxylate esters with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the thio- prefix. They are the product of esterification of a carboxylic acid with a thiol. In biochemistry, the best-known thioesters are derivatives of coenzyme A, e.g., acetyl-CoA. The R and R' represent organyl groups, or H in the case of R.
In organic chemistry, an allyl group is a substituent with the structural formula −CH2−HC=CH2. It consists of a methylene bridge attached to a vinyl group. The name is derived from the scientific name for garlic, Allium sativum. In 1844, Theodor Wertheim isolated an allyl derivative from garlic oil and named it "Schwefelallyl". The term allyl applies to many compounds related to H2C=CH−CH2, some of which are of practical or of everyday importance, for example, allyl chloride.
In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds are cleaved with ozone. Multiple carbon–carbon bond are replaced by carbonyl groups, such as aldehydes, ketones, and carboxylic acids. The reaction is predominantly applied to alkenes, but alkynes and azo compounds are also susceptible to cleavage. The outcome of the reaction depends on the type of multiple bond being oxidized and the work-up conditions.
In chemistry, the term phosphonium describes polyatomic cations with the chemical formula PR+
4. These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions.
Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula (CH2)4NH. It is a cyclic secondary amine, also classified as a saturated heterocycle. It is a colourless liquid that is miscible with water and most organic solvents. It has a characteristic odor that has been described as "ammoniacal, fishy, shellfish-like". In addition to pyrrolidine itself, many substituted pyrrolidines are known.
In organic chemistry, an aza-crown ether is an aza analogue of a crown ether. That is, it has a nitrogen atom in place of each oxygen atom around the ring. While the parent crown ethers have the formulae (CH2CH2O)n, the parent aza-crown ethers have the formulae (CH2CH2NH)n, where n = 3, 4, 5, 6. Well-studied aza crowns include triazacyclononane, cyclen, and hexaaza-18-crown-6.
1,4-Dihydropyridine (DHP) is an organic compound with the formula CH2(CH=CH)2NH. The parent compound is uncommon, but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactors NADH and NADPH are derivatives of 1,4-dihydropyridine. 1,4-Dihydropyridine-based drugs are L-type calcium channel blockers, used in the treatment of hypertension. 1,2-Dihydropyridines are also known.
Fluorobenzene is an aryl fluoride and the simplest of the fluorobenzenes, with the formula C6H5F, often abbreviated PhF. A colorless liquid, it is a precursor to many fluorophenyl compounds.
Methanediol, also known as formaldehyde monohydrate or methylene glycol, is an organic compound with chemical formula CH2(OH)2. It is the simplest geminal diol. In aqueous solutions it coexists with oligomers. The compound is closely related and convertible to the industrially significant derivatives paraformaldehyde, formaldehyde, and 1,3,5-trioxane.
2-Benzylpiperidine is a stimulant drug of the arylpiperidine family. It is similar in structure to certain other stimulants such as methylphenidate and desoxypipradrol. However, it is far less potent as a monoamine reuptake inhibitor in comparison. The drug is little used as a stimulant, with its main use being as a synthetic intermediate in the manufacture of other drugs.
Pempidine is a ganglion-blocking drug, first reported in 1958 by two research groups working independently, and introduced as an oral treatment for hypertension.
Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.
2-Piperidinone is an organic compound with the formula (CH2)4CONH. Valerolactam is formed by dehydrogenation of 5-amino-1-pentanol, catalyzed by rhodium and ruthenium complexes, The compound, a colorless solid, is classified as a lactam.
Nickel(II) nitrite is an inorganic compound with the chemical formula Ni(NO2)2. Anhydrous nickel nitrite was first discovered in 1961 by Cyril Clifford Addison, who allowed gaseous nickel tetracarbonyl to react with dinitrogen tetroxide, yielding a green smoke. Nickel nitrite was the second transition element anhydrous nitrite discovered after silver nitrite.
The fluorenylmethoxycarbonyl protecting group (Fmoc) is a base-labile amine protecting group used in organic synthesis, particularly in peptide synthesis. It is popular for its stability toward acids and hydrolysis and its selective removal by weak bases, such as piperidine, without affecting most other protecting groups or sensitive functional groups. Fmoc protection is especially advantageous in solid-phase peptide synthesis (SPPS), where its compatibility with other reagents and ease of removal streamline synthesis workflows. Upon deprotection, Fmoc yields a byproduct (Dibenzofulvene) that can be monitored by UV spectroscopy, allowing for efficient reaction tracking.
Bispidine (3,7-diazabicyclo[3.3.1]nonane) is an organic compound that is classified as a bicyclic diamine. Although synthetic, it is related structurally to natural alkaloid sparteine. It is a white crystalline solid. It has been widely investigated as a chelating agent. Many derivatives are known.
Transition metal dithiocarbamate complexes are coordination complexes containing one or more dithiocarbamate ligand, which are typically abbreviated R2dtc−. Many complexes are known. Several homoleptic derivatives have the formula M(R2dtc)n where n = 2 and 3.
1-Boc-4-AP is a compound used as an intermediate in the manufacture of fentanyl, as well as various related derivatives such as butyrylfentanyl, furanylfentanyl, benzylfentanyl and homofentanyl, among others. It is an N-protected derivative of 4-anilinopiperidine which can be readily converted to fentanyl or related analogues in several straightforward synthetic steps. It was classified as a DEA List 1 Chemical in 2022, and is also controlled in various other jurisdictions. Its possession, sale and importation are consequently heavily regulated throughout much of the world. 1-Boc-4-AP has also been identified as an impurity in other designer drug products, though it is unclear if it has any pharmacological activity in its own right.