334618-23-4

Basic information

• Product Name: (R)-3-Piperidinamine dihydrochloride
• Synonyms: (R)-PIPERIDIN-3-YLAMINE DIHYDROCHLORIDE;(R)-PIPERIDINE-3-AMINE DIHYDROCHLORIDE;(R)-(-)-3-AMINOPIPERIDINE DIHYDROCHLORIDE;(R)-3-AMINOPIPERIDINE DIHYDROCHLORIDE;(R)-3-PIPERIDINAMINE DIHYDROCHLORIDE;R-3-AMINOPIPERIDINE DIHCL;(R)-(-)-3-AMINOPIPERIDINE 2HCL;(R)-3-AMINOPIPERIDINE 2HCL
• CAS NO: 334618-23-4
• Molecular Formula: C5H14Cl2N2
• Molecular Weight: 173.08406
• EINECS: 1308068-626-2
• Product Categories: pharmacetical;Piperidine;Piperidines;intermediate
• Mol File: 334618-23-4.mol

Chemical Properties

• Melting Point: 190-195 °C
• Boiling Point: 241.9 °C at 760 mmHg
• Flash Point: 100.1 °C
• Appearance: White to tan/Powder
• Storage Temp.: Room temperature.
• Solubility: Methanol (Slightly), Water (Slightly)
• Sensitive: Hygroscopic
• CAS DataBase Reference: (R)-3-Piperidinamine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-Piperidinamine dihydrochloride(334618-23-4)
• EPA Substance Registry System: (R)-3-Piperidinamine dihydrochloride(334618-23-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41-36/37/38-20/21/22
• Safety Statements: 26-39-36/37/39
• WGK Germany: 2
• F: 10-21
• Hazardous Substances Data: 334618-23-4(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

(R)-3-Aminopiperidine Dihydrochloride has been used as a reactant for the preparation of dipeptidyl peptidase IV inhibitors derived from Alogliptin.

Upstream product

• 462-08-8 pyridin-3-ylamine 
• 1352756-67-2 N-acetyl-3-aminopyridine acetate 
• 1353094-64-0 N-acetyl-3-aminopiperidine acetate 
• 1352756-66-1 (R)-piperidine-3-amine dibenzoyl-D-tartrate 
• 184637-48-7 t-butyl piperidin-3-ylcarbamate 
• 397246-12-7 (1,5-dihydroxypent-2-yl)carbamic acid tert-butyl ester 
• 861658-15-3 1,5-dimethyl 2-[(t-butoxycarbonyl)amino]pentanedioate 
• 617-65-2 Glutamic acid 
• 6525-53-7 glutamic acid dimethyl ether 
• 4138-26-5 nipecotamide 
• 1186123-48-7 (R)-isopropyl piperidin-3-ylcarbamate 
• 98977-36-7 3-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 188111-79-7 tert-butyl (3R)3-aminopiperidine-1-carboxylate 
• 54012-73-6 3-aminopiperidine 

Downstream Products

• 1460202-50-9 (S)-3-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propanoic acid (S)-3-aminopiperidine salt 

Relevant articles and documents

Preparation of (R)-3-aminopiperidine by resolution with optically active cyclic phosphoric acids

(R)-3-aminopiperidine ((R)-APD), a key intermediate for alogliptin, trelagliptin, and linagliptin, was successfully resolved from racemic 3-aminopiperidine with an enantiomerically pure resolving agent, namely, (R)-4-(2-chlohydroxy-1.3.2-dioxaphosphorinane 2-oxide ((R)-CPA), via diastereomeric salt formation. By this resolution approach, (R)-3-aminopiperidine was obtained in 99.5% yield with 99.6%e.e.

Synthesis method of trelagliptin intermediate

The invention belongs to the technical field of medicines, and particularly relates to a synthesis method of a trelagliptin intermediate (R)-3-aminopiperidine dihydrochloride. The synthesis method specifically comprises the following steps: 1) reducing carbonyl of a compound shown as a formula I in an organic solvent A by using a reducing agent to prepare a compound shown as a formula II; 2) splitting the compound shown in the formula II in an organic solvent B through a chiral reagent to prepare a compound shown in a formula III; and 3) removing the benzyl of the compound shown by the formula III by palladium on carbon to obtain the (R)-3-aminopiperidine dihydrochloride. The (R)-3-aminopiperidine dihydrochloride prepared by the method has high yield and purity, the HPLC purity is higher than 98.16%, and the optical purity is higher than 98.92%; and the synthesis method has the advantages of low price of initial raw materials, facilitation of reduction of industrial cost, short synthesis process route, mild reaction conditions and easy industrial realization.

Preparation method and application of (R)-3-aminopiperidine dihydrochloride

The invention provides a preparation method and application of (R)-3-aminopiperidine dihydrochloride. The preparation method comprises the following steps: obtaining (S)-1, 5-dichloro-2-pentanol through the reaction of (S)-epichlorohydrin and 2-chloroethyl magnesium bromide; carrying out an intramolecular cyclization reaction in the presence of an alkaline substance to generate (S)-5-chloro-1, 2-epoxypentane; enabling the (S)-1-benzylamino-5-chloro-2-epoxypentane to react with benzylamine to generate (S)-1-benzylamino-5-chloro-2-pentanol; then obtaining (S)-1-benzyl-3-hydroxypiperidine throughan intramolecular ring closing reaction of (S)-1-benzylamino-5-chloro-2-pentanol; continuing to react with the sulfonyl chloride compound to obtain (R)-1-benzyl-3-sulfonyloxy piperidine; further reacting with benzylamine to obtain (R)-1-benzyl-3-benzylamino piperidine; and finally, under the action of a palladium catalyst, removing benzyl through hydrogenation, thus obtaining the product (R)-3-aminopiperidine dihydrochloride. The preparation method has the advantages of few side reactions, high yield, good product quality, convenient purification, easily available raw materials, low price, mild reaction conditions, high safety, environmental protection, simplicity, practicality, and suitableness for industrial batch production.

Synthesis method of chiral 3-aminopiperidine and derivatives of 3-aminopiperidine

The invention relates to a synthesis method of chiral 3-aminopiperidine and derivatives of 3-aminopiperidine. According to the synthesis method, R (or S)-piperidine-3-ethyl formate-L (or D)-tartrate is subjected to a hydrazinolysis reaction after being subjected to benzyl protection, and R or S-1-benzyl-3-aminopiperidine is obtained through azidation and Curtius rearrangement. R or S-1-benzyl-3-aminopiperidine is subjected to debenzylation, R or S-3-aminopiperidine can be obtained, R or S-1-benzyl-3-aminopiperidine is subjected to 3-t-butyloxycarboryl protection and debenzylation in sequence,R or S-(3-t-butyloxycarborylamino) piperidine can be obtained, and corresponding salts of R or S-3-aminopiperidine can be obtained through hydrolyzing deprotection of R or S-(3-t-butyloxycarborylamino) piperidine under the acidic condition. The synthesis method of chiral 3-aminopiperidine and the derivatives of 3-aminopiperidine is low in cost, facilitates industrialization and has high optical purity.

Synthetic process of anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride

The invention relates to a synthetic process of an anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride. The synthetic process comprises the steps: using inexpensive L-glutamic acid as a starting material, and performing esterification, amino protection, reduction, hydroxyl protection, substitution, cyclization and removal of protecting groups for amino groups so as to obtainthe R-3-amino-piperidine dihydrochloride. Compared with the prior art, the synthetic process has cheap and easily available raw materials, good selectivity, good atomic economy, high total yield and mild reaction conditions, and is suitable for industrial production.

Asymmetric synthesis of a high added value chiral amine using immobilized ω-transaminases

Chiral N-heterocyclic molecules and in particular compounds with an amino functional group such as 3-aminopiperidine are valuable intermediates for the production of a large number of bioactive compounds with pharmacological properties. In this paper, the synthesis of both enantiomers of 3-amino-1-Boc-piperidine by amination of the prochiral precursor 1-Boc-3-piperidone using immobilized ω-transaminases (TAs-IMB), isopropylamine as amine donor and pyridoxal-5’-phosphate (PLP) as cofactor is described. Compared to other methods, the present approach affords the target compound in just one step with high yield and high enantiomeric excess starting from a commercial substrate. The reaction was carried out by using different commercially available immobilized enzymes, evaluating the catalytic activity and the enantioselectivity under different experimental conditions. Re-use of the most efficient enzyme was performed both in batch and in a semi-continuous system. The selected biocatalyst showed good stability under the reaction conditions providing consistent results in terms of conversion and enantiomeric excess after several cycles. The reported results may be of practical interest in view of the development of this sustainable approach to an industrial scale.

Method for preparing chiral compound by using intermediate

The invention provides a method for preparing a chiral compound by using an intermediate. The method is characterized by comprising the following steps: (a) enabling a compound II to be contacted witha compound III in a solvent, and refining to obtain a c

A methof for preparing (R)- (+) - 3 - amino piperidine dihydrochloride method

The invention discloses a method for preparing (R)-(+)-3-piperidinamine dihydrochloride by using a resolution method, which belongs to the field of racemic compound resolution. The method is specifically implemented by taking 1-2 equivalent amounts of (+)-4-(2-chlorphenyl)-2-hydroxy-5 and 5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane as resolution agents through enabling the resolution agents to react with racemic 3-aminopiperdine in an alcohol-water solution, so that salt coagulation is realized; reducing the temperature of the obtained object so as to separate out solids, and carrying out dissociation on the solids, so that optical pure (R)-(+)-3-aminopiperidinedihydrochloride is obtained; and carrying out dissociation on mother liquor so as to recover (S)-(-)-3-aminopiperidinedihydrochloride, carrying out racemization on the (S)-(-)-3-aminopiperidinedihydrochloride, and recycling the obtained product. The method is simple in operation, and a resolution reagent can be recycled, therefore, the method is suitable for industrial production.

Compound I and (R)- 3 - amino piperidine hydrochloride II, its preparation method and its application in the synthesis of advantage geleg sandbank

The invention discloses a preparation method of 3-aminopiperidine and its derivative with optical activity and an application of the compound and its derivative in synthesis of a dipeptidyl peptidase-IV inhibitor Linagliptin. According to the preparation

Application of asymmetric hydrogenation in synthesis of Trelagliptin intermediate

The invention provides a synthetic method of a compound Trelagliptin intermediate represented by a formula (1) (shown in the description). The synthetic method comprises the steps of carrying out a series of reactions on a starting material, namely a compound represented by a formula (1) (shown in the description) so as to finally obtain the compound by the formula (1), namely the Trelagliptin intermediate. Compared with a synthetic method of the Trelagliptin intermediate which comprises more synthetic steps and has a complex synthetic process in the prior art, the synthetic method provided by the invention is simple, feasible, relatively low in cost, relatively high in yield, relatively good in product quality and suitable for large-scale industrial production.