190730-41-7

Basic information

• Product Name: 1-Piperidinebutanoic acid, 4-[(4-chlorophenyl)-2-pyridinylmethoxy]-, (R)-
• Synonyms: 1-Piperidinebutanoic acid, 4-[(4-chlorophenyl)-2-pyridinylmethoxy]-, (R)-;1-Piperidinebutanoic acid, 4-[(R)-(4-chlorophenyl)-2-pyridinylmethoxy]-;(R)-Bepotastine
• CAS NO: 190730-41-7
• Molecular Formula: C21H25 Cl N2 O3
• Molecular Weight: 388.89
• Mol File: 190730-41-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Piperidinebutanoic acid, 4-[(4-chlorophenyl)-2-pyridinylmethoxy]-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinebutanoic acid, 4-[(4-chlorophenyl)-2-pyridinylmethoxy]-, (R)-(190730-41-7)
• EPA Substance Registry System: 1-Piperidinebutanoic acid, 4-[(4-chlorophenyl)-2-pyridinylmethoxy]-, (R)-(190730-41-7)

Safety Data

• Hazardous Substances Data: 190730-41-7(Hazardous Substances Data)

Usage

Enantiomer

(R)form, indicating the specific three-dimensional arrangement of the molecule

Rotating plane-polarized light

The (R)-enantiomer rotates plane-polarized light in a specific direction, which is important in the field of optical activity

Piperidine ring

A nitrogen-containing six-membered aromatic ring, which is a common structural motif in many pharmaceuticals

Butanoic acid group

A four-carbon carboxylic acid, contributing to the acidic properties of the compound

4-[(4-chlorophenyl)-2-pyridinylmethoxy] substituent

A functional group attached to the piperidine ring, which includes a chlorine atom and a pyridine ring connected through an oxygen atom

Potential applications

1-Piperidinebutanoic acid, 4-[(4-chlorophenyl)-2-pyridinylmethoxy]-, (R)- may have potential applications in pharmaceuticals, as compounds with similar structures have been studied for their biological activities, such as antipsychotic and anti-inflammatory properties

Further research

More research is needed to fully understand the specific properties and potential uses of this particular compound, including its pharmacokinetics, pharmacodynamics, and safety profile.

Upstream product

• 176022-47-2 (S)-(+)-(4-chlorophenyl)-(2-pyridyl)methanol 
• 180695-79-8 tert-butyl 4-bromo-1-piperidinecarboxylate 
• 301673-14-3 tert-butyl 4-iodopiperidine-1-carboxylate 
• 190786-43-7 4-(4-[(4-chlorophenyl)-pyridin-2-ylmethoxy]piperidin-1-yl)butanoic acid 
• 142404-69-1 2-[chloro(4-chlorophenyl)methyl]pyridine 
• 125602-67-7 ethyl 3-[4-[(4-chlorophenyl)-pyridin-2-ylmethoxy]-1-piperidyl]propionate 
• 27652-89-7 (4-chlorophenyl)-2-pyridylmethanol 
• 207726-35-0 4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine-1-carboxylic acid ethyl ester 
• 6318-51-0 2-(4-chlorobenzoyl)pyridine 

Relevant articles and documents

Total synthesis method of bestatin

The method comprises the following steps: (4 - chlorophenyl) (2 - pyridyl) - methanol as a starting raw material, and sequential addition reaction. Examples of the etherification reaction include a deprotection reaction, a chiral resolution, a condensation reaction, a hydrolysis reaction, and the like. The synthesis method has the advantages of cheap and easily available raw materials, no need of expensive chiral catalysts, simpler synthesis method, mild conditions, less side reactions and low cost.

Identification, Characterization and HPLC Quantification of Process-Related Impurities in Bepotastine Besilate Bulk Drug

Bepotastine besilate (here after referred to as BTST), chemically known as ({d(S)4[4[(4chlorophenyl) (2pyridyl) methoxy] piperidino} butyric acid monobenzene sulphonate), is a second-generation antihistamine drug. To the best of our knowledge, no studies concerning the isolation or identification of process-related impurities have been reported so far. The current study reports the development and validation of a stability-indicating RP-HPLC method for the separation and identification of 5 potential impurities in bepotastine besilate. In this experiment, the structures of 3 process-related impurities were found to be new compounds. They were characterized and confirmed by NMR and MS spectroscopy analyses. These 3 new compounds were proposed to be (S)-4-[(phenyl)-2-pyridinylmethoxy]-1-piperidinebutanoic acid,(Imp-A); 4-[(S)-(4-chlorophenyl)-2-pyridinylmethoxy]-1- piperidinebutyric acid, N-oxide (Imp-B) and (S)-4-[(4- chlorophenyl)-2-pyridinylmethoxy]-1-piperidylethane (Imp-C). In addition, an efficient optimized chromatographic method was performed on a Shimadzu Inertsil C8-3 column (150 mm×4.6 mm, 3 μm) to separate and quantify these 5 impurities. It was using 15 mmol ammonium formate buffer in water (pH adjusted to 3.8 with formic acid) and acetonitrile as the mobile phase in gradient mode. The method was developed to separate and quantify these 5 impurities obtained in the range of 0.05-0.75 μg/mL. It was validated and proven to be selective, accurate and precise and suitable. It is the first publication of identification and characterization data of the 3 new compounds. It is also the first effective HPLC method for separation and quantification of all of process-related impurities in bepotastine besilate.

METHOD FOR MAKING PIPERIDINE DERIVATIVE INTO RACEMATE

PROBLEM TO BE SOLVED: To provide a method for making efficiently a (R)-piperidine derivative into a racemate, and a method for producing a (S)-piperidine derivative from the racemate. SOLUTION: A method for producing a piperidine derivative of a racemate

Asymmetric syntheses method of ophthalmologic drug bepotastine besilate

The invention relates to an asymmetric synthesis method of an ophthalmologic drug pylistramine besylate. The method concretely comprises the following steps: oxidizing (4-chlorophenyl)(2-pyridyl)methanone to obtain (4-chlorophenyl)(2-pyridyl)ketone-N-oxide; carrying out asymmetric transfer hydrogenation reduction on the (4-chlorophenyl)(2-pyridyl)ketone-N-oxide through using a complex of monosulfonyl chiral diamine and metallic ruthenium, rhodium and iridium as a catalyst and a sodium formate or formic acid and triethylamine mixture or isopropanol as a hydrogen source in order to prepare (S)-(4-chlorophenyl)(2-pyridyl)methanol-N-oxide; reducing the (S)-(4-chlorophenyl)(2-pyridyl)methanol-N-oxide to prepare (S)-(4-chlorophenyl)(2-pyridyl)methanol; and condensing the (S)-(4-chlorophenyl)(2-pyridyl)methanol and ethyl 4-(4-bromopiperidine-1-yl)butyrate to obtain the ophthalmologic drug pylistramine besylate. The total yield is 61.6%.

Novel chiral resolving agent and Method for optically resolving preparation of (RS)-Bepotastine using thereof

The present invention relates to a method for optically resolving (RS)-bepotastine by directly optically resolving (RS)-bepotastine by using an optical resolution agent. Different to a conventional method of optically resolving (RS)-bepotastine by attaching a subsidiary group having optical activity to the end of the (RS)-bepotastine, the method for optically resolving (RS)-bepotastine according to the present invention is a novel preparation method for directly optically resolving (RS)-bepotastine by using an optical resolution agent only. The method of the present invention optically resolves (RS)-bepotastine into (S)-bepotastine with high yield and high optical purity.

Improved preparation method of bepotastine besilate

The invention relates to an improved preparation method of bepotastine besilate.The improved preparation method of bepotastine besilate includes the following steps that firstly, 2-[(4-chlorophenyl)(4-piperidinyloxy)methyl]pyridine and a resolving agent a

OPTICALLY ACTIVE PIPERIDINE DERIVATIVE ACID-ADDITION SALT AND PREPARATION THEREOF

PROBLEM TO BE SOLVED: To provide a benzene sulfonic acid salt of (S)-4-[4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidino]butanoic acid, that is excellent in anti-histaminic activity and anti-allergic activity, is low in acid addition salt hygroscopic property, and is excellent in physicochemical stability, and to provide a preparation thereof. SOLUTION: Provided is a benzene sulfonic acid salt of an optically active piperidine derivative, represented by formula (I), whose absolute configuration is in (S) form. Also provided is a synthesis method in which an optically active (S)-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine (IV) obtained by inducing an intermediate (±)-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine into a diastereomeric salt and optically resolving the same by fractional crystallization method, is used as the intermediate. COPYRIGHT: (C)2016,JPOandINPIT

Preparation method of anti-allergic drug bepotastine

The invention discloses a preparation method of an anti-allergic drug bepotastine, and relates to the technical field of anti-allergic drugs. The technical point of the invention is that a compound (S)-(4-chlorophenyl)(2-pyridyl)-methanol (formula II) is adopted as an initial raw material and is subjected to a reaction with N-tert-butoxycarbonyl-4-halopiperidine, such that a compound (S)-N-tert-butoxycarbonyl-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine (formula III) is obtained; under an acidic condition, the protecting group of the compound represented by the formula (III) is removed, such that a compound (S)-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine (formula IV) is obtained; the compound represented by the formula (IV) is subjected to a nucleophilic substitution reaction with 4-chlorobutanamide, such that a compound (S)-4-[(4-chlorophenyl)(2-pyridyl)methoxy]-piperidinyl]-butyramide (formula V) is obtained; the amide group of the compound represented by the formula (V) is hydrolyzed, such that the target product which is the anti-allergic drug bepotastine is obtained. The method provided by the invention has the advantages of simple synthesis route and low cost, and is suitable for large-scale production of the optically pure anti-allergic drug bepotastine.