154477-55-1

Basic information

• Product Name: Methyl-4-4(4-hydroxy diphenyl-methyl)-piperidine-1-oxobutyl-2-2-dimethyl phenyl
• Synonyms: Methyl-4-4(4-hydroxy diphenyl-methyl)-piperidine-1-oxobutyl-2-2-dimethyl phenyl;2-[4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]-2,2-dimethylacetic acid methyl ester;METHYL-4-4(4-HYDROXY DIPHENYL-METHYL)-PIPERIDINE-1-OXOBUTYL-2-2-DIMETHYL PHENYL ACETIC ACID;Methyl 2-(4-(4-(4-(hydroxydiphenylMethyl)piperidin-1-yl)butanoyl)phenyl)-2-Methylpropanoate;Methyl 2-(4-(4-((4-((4-hydroxyphenyl)(phenyl)methyl)-piperidin-1-yl)oxy)butyl)phenyl)-2-methylpro;1-Oxo Fexofenadine Methyl Ester;Methyl 4- 4- 4-(hydroxydiphenylMethyl)-1-piperidinyl -1-butyryl -alpha, alpha-diMethylbenzene acetate;Methyl 2-(4-(4-((4-((4-hydroxyphenyl)(phenyl)Methyl)piperidin-1-yl)oxy)butyl)phenyl)-2-Methylpropanoate
• CAS NO: 154477-55-1
• Molecular Formula: C₃₃H₃₉NO₄
• Molecular Weight: 513.674
• EINECS: 1312995-182-4
• Mol File: 154477-55-1.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 657.185 °C at 760 mmHg
• Flash Point: 351.253 °C
• Appearance: /
• Density: 1.131
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: 2-8°C
• PKA: 13.32±0.29(Predicted)
• CAS DataBase Reference: Methyl-4-4(4-hydroxy diphenyl-methyl)-piperidine-1-oxobutyl-2-2-dimethyl phenyl(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-4-4(4-hydroxy diphenyl-methyl)-piperidine-1-oxobutyl-2-2-dimethyl phenyl(154477-55-1)
• EPA Substance Registry System: Methyl-4-4(4-hydroxy diphenyl-methyl)-piperidine-1-oxobutyl-2-2-dimethyl phenyl(154477-55-1)

Safety Data

• Hazardous Substances Data: 154477-55-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Methyl-4-4(4-hydroxy diphenyl-methyl)-piperidine-1-oxobutyl-2-2-dimethyl phenyl is used as a research compound for exploring its potential medicinal properties. Its unique structure, including the piperidine, butyl, and dimethylphenyl groups, as well as the hydroxy and diphenylmethyl moieties, may offer valuable insights into the development of new drugs or therapeutic agents.
Used in Industrial Applications:
In the industrial sector, Methyl-4-4(4-hydroxy diphenyl-methyl)-piperidine-1-oxobutyl-2-2-dimethyl phenyl may be employed as a functional chemical for specific purposes. Its complex structure and the presence of various functional groups could provide it with unique properties that are beneficial in certain applications, such as in the synthesis of other compounds or as an intermediate in chemical processes.

InChI:InChI=1/C33H39NO4/c1-32(2,31(36)38-3)26-18-16-25(17-19-26)30(35)15-10-22-34-23-20-29(21-24-34)33(37,27-11-6-4-7-12-27)28-13-8-5-9-14-28/h4-9,11-14,16-19,29,37H,10,15,20-24H2,1-3H3

Upstream product

• 154825-95-3 4-<4-<4-(Hydroxydiphenylmethyl)-1-piperidinyl>-1-butynyl>-α,α-dimethylbenzeneacetic acid methyl ester 
• 108-86-1 bromobenzene 
• 4559-96-0 1-(4-bromophenyl)-4-chlorobutan-1-one 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 547-63-7 Methyl isobutyrate 
• 140-29-4 phenylacetonitrile 
• 169280-21-1 2-[4-(4-chloro-butyryl)-phenyl]-2-methyl-propionic acid 
• 169280-15-3 2-[4-(4-Chloro-butyryl)-phenyl]-2-methyl-propionic acid , N-methoxy-N-methylamide 
• 169280-16-4 2-methyl-2-phenyl-propionic acid , N-methoxy-N-methylamide 
• 826-55-1 2-methyl-2-phenylpropionic acid 
• 36293-05-7 2-methyl-2-phenylpropanoyl chloride 
• 1195-98-8 2-methyl-2-phenylpropionitrile 
• 115-46-8 C₁₈H₂₁NO 
• 394222-31-2 methyl 4-(4-bromo-1-oxobutyl)-α,α-dimethylphenylacetate 

Downstream Products

• 154825-96-4 fexofenadine methyl ester 
• 83799-24-0 fexofenadine 
• 76811-98-8 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid 

Relevant articles and documents

Preparation method of fexofenadine

The invention provides a preparation method of fexofenadine, which comprises the following steps: by using bromobenzene as a raw material, carrying out Friedel-Crafts acylation reaction to obtain 4'-bromo-4-chlorophenone ; enabling 4'-bromo-4-chlorobutanone and 1-methoxy-1-(trimethylsiloxy)-2-methyl-1-propene to subjected to coupling reaction to obtain 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methyl methyl propionate; and sequentially carrying out N-alkylation, carbonyl reduction and alkaline hydrolysis on 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methylpropanoate to obtain fexofenadine. The method has the advantages of cheap and easily available raw materials, easiness in operation, high yield, low cost, no meta-isomer, suitability for industrial production and the like.

Synthetic method of fexofenadine intermediate

The invention provides a synthetic method of a fexofenadine intermediate 2-[4-[4-[4-(hydroxybenzhydryl)-1-piperidyl]-butyryl]phenyl]-2- methylmethacrylate. The method comprises the following steps: methylation of phenylacetonitrile which is used as a raw material, basic hydrolysis, weinreb amidation reaction, Friedel-crafts reaction, acid hydrolysis, esterification and condensation. The method has the following advantages: raw materials and auxiliary materials are cheap and easily available; yield is high; cost is low; there is no meta-isomer; and the method is suitable for industrial production.

METHODS AND COMPOSITIONS FOR TREATING INFECTION

Provided herein are compositions and methods for treating or preventing infection.

Repurposing the antihistamine terfenadine for antimicrobial activity against staphylococcus aureus

Staphylococcus aureus is a rapidly growing health threat in the U.S., with resistance to several commonly prescribed treatments. A high-throughput screen identified the antihistamine terfenadine to possess, previously unreported, antimicrobial activity against S. aureus and other Gram-positive bacteria. In an effort to repurpose this drug, structure-activity relationship studies yielded 84 terfenadine-based analogues with several modifications providing increased activity versus S. aureus and other bacterial pathogens, including Mycobacterium tuberculosis. Mechanism of action studies revealed these compounds to exert their antibacterial effects, at least in part, through inhibition of the bacterial type II topoisomerases. This scaffold suffers from hERG liabilities which were not remedied through this round of optimization; however, given the overall improvement in activity of the set, terfenadine-based analogues provide a novel structural class of antimicrobial compounds with potential for further characterization as part of the continuing process to meet the current need for new antibiotics.

INTERMEDIATES USEFUL FOR THE SYNTHESIS OF FEXOFENADINE, PROCESSES FOR THEIR PREPARATION AND FOR THE PREPARATION OF FEXOFENADINE

Intermediates useful for the synthesis of fexofenadine, processes for their preparation and processes for the synthesis of fexofenadine are described.

Process for Preparing Fexofenadine

A process for preparing fexofenadine is described that includes the purification of 4-[4-chloro-1-oxobutyl]-2,2-dimethylphenyl acetic acid alkyl ester by means of suspension in a hydrocarbon, preferably n-heptane. The compound thus obtained is dissolved in a suitable solvent and condensed with azacyclanol to give the compound shown below where R is an alkyl radical, which is then hydrolysed and reduced to give fexofenadine.

PROCESS FOR THE PREPARATION OF KETO INTERMEDIATES

Process for the preparation of 4-[1-oxo-4-[4-(hydroxyphenylmethyl)-1-piperidinyl]butyl]-α,α-dimethylbenzenacetic acid, which is an intermediate useful in the preparation of fexofenadine, by hydrating asymmetric alkynes.

PROCESS FOR PREPARATION OF 4-[4-(4-(HYDROXYDIPHENYLMETHYL)- 1-PIPERIDINYL]-1-OXOBUTYL]-α,α-DIMETHYLBENZENE ACETIC ACID METHYL ESTER AND USE THEREOF

The present invention provides an improved process for preparing fexofenadine, its pharmaceutically acceptable salts and solvates thereof, the process comprising reacting methyl-4-(4-halo-1-oxobutyl]-α,α-dimethylphenyl acetate with α,α-diphenyl-4-piperidinemethanol in an alkyl nitrile solvent to prepare 4-[4-(4- (hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α,-dimethylbenzene acetic acid alkyl ester, which is further converted into fexofenadine.

PROCESS FOR PREPARING FEXOFENADINE

A process for preparing fexofenadine is described, comprising the purification of 4-[4-chloro-l-oxobutyl]-2,2-dimethylphenyl acetic acid alkyl ester by means of suspension in a hydrocarbon, preferably n-heptane. The compound thus obtained is dissolved in a suitable solvent and condensed with azacyclanol to give the compound shown below (I) where R is an alkyl radical, which is then hydrolysed and reduced to give fexofenadine.

INDUSTRIAL PROCESS OF FEXOFENADINE HYDROCHLORIDE WITH CONTROLLED SIDE PRODUCTS

The present invention relates to a process for the preparation of Anhydrous Fexofenadine Hydrochloride with controlled level of side products. Another aspect of the present invention is purification of Fexofenadine base free of meta isomer of fexofenadine base and fexofenadinone.