1-Acetyl-4-piperidinecarboxylic acid #CAS25503-90-6

1-Acetyl-4-piperidinecarboxylic acid #CAS25503-90-6

It is a six-membered nitrogen-containing heterocyclic compound that combines both aliphatic carboxylic acid and tertiary amide structures. Its chemical activity is mainly concentrated on the carboxyl group at the top, and it can undergo efficient esterification, amide formation, or acyl halide reactions with alcohols, amines, or halogenating agents. It is often used as a core synthetic building block for introducing the "1-acetyl-4-piperidyl" protection framework. The nitrogen atom on the piperidine ring is significantly less basic and nucleophilic than ordinary piperidine due to being locked by the strong electron-withdrawing acetyl group (amide bond). It exhibits good chemical stability against oxidants and common electrophilic reagents at room temperature. When heated in a strong acid or strong base aqueous solution, the amide bond can undergo hydrolysis, removing the acetyl group and reducing to the free 4-piperidyl formic acid. Additionally, this substance exhibits typical properties of solid carboxylic acids and can form salts with inorganic bases. When decomposed under high heat, it releases irritating nitrogen oxides (NOₓ) harmful smoke.

Application Of 1-Acetyl-4-piperidinecarboxylic acid

A synthetic intermediate in the preparation of CNS depressants.

Reactant for synthesis of:• ;Triazole derivatives1• ;Antiproliferative agents2• ;CDK inhibitors3• ;CCR5 antagonists for HIV treatment4• ;nhNK1 antagonists5• ;Piperidine derivatives6.

Metabolite fingerprinting in transgenic Nicotiana tabacum altered by the Escherichia coli glutamate dehydrogenase gene.

It is a high-end pharmaceutical intermediate and functional modification building block with significant application value. Its most crucial industrial application lies in the pharmaceutical industry, where it is used to synthesize a series of antithrombotic drugs, anti-arrhythmic drugs, and complex drugs targeting the central nervous system. Through the precise amidation reaction at the top active carboxyl group of its molecule, it can efficiently introduce the "1-acetyl-4-piperidine" structural fragment with metabolic stability into the drug molecule targets, thereby optimizing the bioavailability and pharmacological activity of the drug molecules. Moreover, due to its excellent coordination potential, this substance is also widely used as a new type of heterocyclic functional monomer in the industrial research and development of advanced materials such as modern electronic chemicals, special polymer modifiers, and fine chemical sensors.

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