169280-21-1

Basic information

• Product Name: 4-(4-Chloro-1-oxobutyl)-α,α-dimethylbenzeneacetic acid
• Synonyms: 4-(4-Chloro-1-oxobutyl)-a,a-dimethylbenzeneacetic acid;4-(4-Chloro-1-oxobutyl)-α,α-dimethylbenzeneacetic acid;4-(4-Chloro-1-oxobutyl)-|á,|á-dimethylbenzeneacetic acid;Benzeneacetic acid, 4-(4-chloro-1-oxobutyl)-a,a-diMethyl-;2-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acid
• CAS NO: 169280-21-1
• Molecular Formula: C₁₄H₁₇ClO₃
• Molecular Weight: 268.73598
• Mol File: 169280-21-1.mol

Chemical Properties

• Boiling Point: 438.1±35.0 °C(Predicted)
• Appearance: /
• Density: 1.185±0.06 g/cm3(Predicted)
• PKA: 4.16±0.10(Predicted)
• CAS DataBase Reference: 4-(4-Chloro-1-oxobutyl)-α,α-dimethylbenzeneacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Chloro-1-oxobutyl)-α,α-dimethylbenzeneacetic acid(169280-21-1)
• EPA Substance Registry System: 4-(4-Chloro-1-oxobutyl)-α,α-dimethylbenzeneacetic acid(169280-21-1)

Safety Data

• Hazardous Substances Data: 169280-21-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Chloro-1-oxobutyl)-α,α-dimethylbenzeneacetic acid serves as a pharmaceutical intermediate, playing a crucial role in the synthesis of various medicinal compounds. Its chemical structure and properties are particularly advantageous for the development of drugs aimed at treating pain and inflammation, making it a key component in the formulation of therapeutic agents for these conditions.

Upstream product

• 169280-04-0 1-[4-(1-Bromo-1-methyl-ethyl)-phenyl]-4-chloro-butan-1-one 
• 124-38-9 carbon dioxide 
• 169280-05-1 1-[4-(1-Chloro-1-methyl-ethyl)-phenyl]-4-chloro-butan-1-one 
• 201230-82-2 carbon monoxide 
• 873072-14-1 1-[4-(1-hydroxy-1-methyl-ethyl)-phenyl]-4-chloro-butan-1-one 
• 28509-24-2 tert-butylmethyl ether 
• 826-55-1 2-methyl-2-phenylpropionic acid 
• 506-59-2 N,N-dimethylammonium chloride 
• 169280-16-4 2-methyl-2-phenyl-propionic acid , N-methoxy-N-methylamide 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 169032-17-1 2-[4-(4-chloro-butyryl)-phenyl]-2-methyl-propionitrile 
• 192775-98-7 4-(4-chloro-1-oxobutyl)-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl) toluene 
• 1195-98-8 2-methyl-2-phenylpropionitrile 
• 36293-05-7 2-methyl-2-phenylpropanoyl chloride 

Downstream Products

• 76811-97-7 4-(4-chloro-1-oxobutyl)-α,α-dimethylbenzeneacetic acid ethyl ester 
• 154477-54-0 2-[4-(4-Chloro-butyryl)-phenyl]-2-methyl-propionic acid, methyl ester 
• 192885-13-5 4-(1-hydroxy-4-chlorobutyl)-α,α-dimethylphenylacetic acid 
• 880088-78-8 2-(4-cyclopropanecarbonyl-phenyl)-2-methyl-propionic acid, methyl ester 
• 154477-55-1 methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate 
• 83799-24-0 fexofenadine 
• 76811-98-8 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid 

Relevant articles and documents

A fexofenadine and method for synthesizing intermediate

The invention relates to a simple and efficient synthetic method of fexofenadine (chemical name: 4-{1-hydroxyl-4-[4-(hydroxyl benzhydryl)-1-piperidyl]-butyl}-alpha, alpha-dimethyl-phenylacetic acid (I)) and its intermediate. According to the method, isopropyl benzene is used as a raw material. Through a Friedel-Crafts acylation reaction, a halogenation reaction and a carbonyl insertion reaction, a key intermediate 4-(4-chloro-1-butyryl)-alpha, alpha-dimethyl phenylacetic acid (IV) is obtained; the key intermediate reacts with another raw material dibenzyl-(4-pyridyl)-methanol (E) to obtain a key pyridinium intermediate 4-{4-chloro-[4-hydroxydiphenylmethyl]-1-pyridinium]-1-butyryl}-alpha, alpha-dimethyl phenylacetic acid (V); and through catalytic hydrogenation and metallic hydrogen reduction, high-purity fexofenadine is obtained. The synthetic method provided by the invention has advantages of smooth process, simple reaction, short route, convenient post-treatment, high yield and low cost, and is a very ideal preparation method of fexofenadine and industrialization feasible route.

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.

PROCESS FOR CARBONYLATING PHENYLALKYL DERIVATIVES BY MEANS OF CARBON MONOXIDE

The invention is directed a process of preparing a compound of formula (I), wherein R1, R2, R3 and z are as defined herein.

METHOD FOR CARBONYLATING PHENYLALKYL DERIVATIVES BY MEANS OF CARBON MONOXIDE

The invention relates to a method for producing a phenylalkyl carboxylic acid of general formula (I), wherein identical or different R1 and R2 represent independently of each other -(C1-C4)-alkyl, Z is a hydrogen atom or -(CH2) n-CH3, wherein n=0 to 9, and R3 is-C(0)-(C1-C4)-alkyl which is substituted or not-substituted by CI or Br, only, or -C(0)-(C3-C6)-cycloalkyl, consisting in reacting a compound of formula (II), wherein X is Cl or Br or OH and R4 is defined as R2 rest represents jointly with X a C-C double bond with a carbon monoxide in the presence of a concentrated sulphuric acid, hydrogen fluoride or peracids and subsequently in adding water or alcohol of the formula CH3-(CH2)n-OH, wherein n=0 to 9.

FEXOFENADINE POLYMORPHS AND PROCESSES OF PREPARING THE SAME

Anhydrous crystalline fexofenadine hydrochloride Form C, crystalline fexofenadine acetate monohydrate Form D, crystalline fexofenadine acetate dihydrate Form E and crystalline fexofenadine free base monohydrate Form F, processes of preparing the same, pharmaceutical compositions thereof, therapeutic uses thereof and methods of treatment therewith.

Intermediates useful for the preparation of antihistaminic piperidine derivatives

The present invention is related to a novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of the formula whereinW represents —C(=O)— or —CH(OH)—;R1 represents hydrogen or hydroxy;R2 represents hydrogen;R1 and R2 taken together form a second bond between the carbon atoms bearing R1 and R2;n is an integer of from 1 to 5;m is an integer 0 or 1;R3 is —COOH or —COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched each of A is hydrogen or hydroxy; andpharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R1 and R2 are taken together to form a second bond between the carbon atoms bearing R1 and R2 or where R1 represented hydroxy, m is an integer 0.

Intermediates useful for the preparation of antihistaminic piperidine derivatives

The present invention is related to a novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of the formula whereinW represents —C(=O)— or —CH(OH)—;R1 represents hydrogen or hydroxy;R2 represents hydrogen;R1 and R2 taken together form a second bond between the carbon atoms bearing R1 and R2;n is an integer of from 1 to 5;m is an integer 0 or 1;R3 is —COOH or —COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched each of A is hydrogen or hydroxy; and pharmaceutically acceptable salts and individual optical isomers thereof,with the proviso that where R1 and R2 are taken together to form a second bond between the carbon atoms bearing R1 and R2 or where R1 represented hydroxy, m is an integer 0.

Process for production of piperidine derivatives

The present invention relates to a method for preparing piperidine derivative compounds by converting, with a piperidine compound, regioisomers having the formula: and where m is an integer from 1 to 6; Q and Y are the same or different and are selected from the group consisting of O, S, and NR5; G1, G2, and G3 are the same or different and are selected from the group consisting of OR8, SR8, and NR8R9; R6 and R7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR8, SR8, and NR8R9; X3 is halogen, OR15, SR15, NR15R16, OSO2R15, or NHSO2R15; R5, R8, R9, R15, and R16 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety; and A is a substituent of its ring and is selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents.

Intermediates useful for the preparation of antihistaminic piperidine derivatives

The present invention is related to a novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of the formula wherein W represents -C(=O)- or -CH(OH)-; R1 represents hydrogen or hydroxy; R2 represents hydrogen; R1 and R2 taken together form a second bond between the carbon atoms bearing R1 and R2; n is an integer of from 1 to 5; m is an integer 0 or 1; R3 is -COOH or -COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched each of A is hydrogen or hydroxy; and pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R1 and R2 are ta to form a second bond between the carbon R1 and R2 or where R1 represented hydroxy integer 0.

Process for production of piperidine derivatives

The present invention relates to a method for preparing piperidine derivative compounds by converting, with a piperidine compound, regioisomers having the formula: where Z is -CG1G2G3, and where m is an integer from 1 to 6; Q and Y are the same or different and are selected from the group consisting of O, S, and NR5; G1, G2, and G3 are the same or different and are selected from the group consisting of OR8, SR8, and NR8R9; and R5, R8, and R9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety.