(R)-3-ピペリジンアミン二塩酸塩

Model:334618-23-4

(R)-3-アミノピペリジン二塩酸塩 (CAS 334618-23-4) は、(R)-3-アミノピペリジンの二塩酸塩であり、R 配置の 3 位に第一級アミンを持つキラルなピペリジン骨格を特徴としています。この分子は、C3 に遊離アミノ基をもつ 6 員ピペリジン環から構成され、2 つの塩化物対イオンによってプロトン化され安定化されています。分子式 C5H14Cl2N2、分子量 173.08 g/mol。

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製品説明

(R)-3-Aminopiperidine Dihydrochloride is a critical chiral intermediate in the synthesis of several clinically important drug classes, most notably dipeptidyl peptidase‑4 (DPP‑4) inhibitors such as alogliptin and other gliptin‑class antidiabetic agents. The free primary amine of (R)-3-Aminopiperidine Dihydrochloride enables diverse chemical transformations including acylation, reductive amination, sulfonylation, and urea formation—reactions fundamental to medicinal chemistry and API synthesis. As a chiral compound with established absolute configuration, (R)-3-Aminopiperidine Dihydrochloride is indispensable for maintaining enantiopurity in pharmaceutical manufacturing. In quality control contexts, it serves as an impurity reference standard for analytical method development and QC testing. The compound is also employed as a building block in the synthesis of novel fine chemicals, agrochemicals, and chemical auxiliaries. With its high water solubility and crystalline nature, (R)-3-Aminopiperidine Dihydrochloride offers excellent handling characteristics for both research and production.

Product Parameter

Parameter	Specification
Product Name	(R)-3-Aminopiperidine Dihydrochloride
CAS Number	334618234
Molecular Formula	C₅H₁₄Cl₂N₂
Molecular Weight	173.08 g/mol
Appearance	White to light yellow powder to crystal
Melting Point	206.0–210.0 °C
Water Solubility	Soluble
Storage Condition	Room temperature,Inert atmosphere

Application

(R)-3-aminopiperidine dihydrochloride has been used as a reactant for the preparation of dipeptidyl peptidase IV inhibitors derived from alogliptin.

Used as a reactant for N-arylation of heterocyclic diamines in reagents; a reactant for the synthesis of substituted quinolones, which can reduce the risk of phototoxicity.

Synthetic Route

There are several main synthetic methods for (R)-3-aminopiperidine dihydrochloride: 1. Using 3-aminopyridine as the starting material, racemic 3-aminopiperidine is obtained via catalytic hydrogenation reduction, and then resolved with a chiral reagent to obtain (R)-3-aminopiperidine. This method has a low yield, and requires an autoclave and expensive catalysts for the catalytic reduction of 3-aminopyridine, which is relatively difficult in actual operation; 2. Using D-ornithine hydrochloride as the starting material, it reacts with thionyl chloride at a temperature between -78 and 45℃, and the crude (R)-3-aminopiperidin-2-one is obtained through a strongly basic anion exchange resin. After purification, it is reduced to (R)-3-aminopiperidine with LiAlH4, and finally converted into the hydrochloride salt. This method uses the chiral raw material ornithine as the starting material, but racemization occurs during the synthesis process. Meanwhile, ornithine is expensive, the reaction is carried out at a deep low temperature (-78℃), which leads to poor operability. In addition, the easily explosive lithium aluminum hydride from Chemicalbook is used, which increases the operating cost; 3. Using nicotinamide as the raw material, the target product is obtained through catalytic hydrogenation reduction, Boc protection, Hofmann degradation, chiral resolution, and deprotection to form the hydrochloride salt. The reaction conditions of this route are milder than those of the previous several routes. Although the conditions for the catalytic hydrogenation of nicotinamide are relatively harsh, there is great room for improvement; 4. Using racemic 3-piperidinecarboxamide as the raw material, (S)-3-piperidinecarboxamide is decomposed by the bacterium (Cupriavidus sp. KNK-J915) to obtain (R)-3-piperidinecarboxamide, which is then subjected to Boc protection of the amino group, Hofmann degradation, and deprotection to form the hydrochloride salt. This method is relatively novel: the bacterium (Cupriavidus sp. KNK-J915) decomposes the S-configuration isomer as a carbon source to obtain the R-configuration isomer of the opposite configuration. However, the separation process for bacterial decomposition has very high requirements and the operating cost is high, so it is temporarily difficult to realize large-scale industrial production at present.

Product Advantages

Chiral primary amine – Enables diverse derivatisation (acylation, alkylation, reductive amination, urea formation).

Dihydrochloride salt – Exceptional water solubility, improved crystallinity, and enhanced storage stability.

Key DPP‑4 inhibitor intermediate – Essential building block for alogliptin and other gliptins.

Versatile utility – Also used in agrochemicals, fine chemicals, and chemical auxiliaries.

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Need (R)-3-Aminopiperidine Dihydrochloride for your DPP‑4 inhibitor program? Cosperpharm is your source for high‑quality chiral intermediates. Contact us today—we‘re ready to support your research, development, and production needs.

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