76811-98-8

Basic information

• Product Name: Fexofenadinone
• Synonyms: 4-((4-(4-Hydroxydiphenylmethyl)-1-piperidinyl)-1-oxobutyl)-a,a-dimethyl-phenylacetic acid;Fexofenadinone;Fexofenadine Related Compound A (25 mg) (4-[1-oxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-alpha,alpha-dimethyl benzeneacetic acid);2-[4-[4-[4-(HydroxydiphenylMethyl)-1-piperidinyl]-1-oxobutyl]phenyl]-2,2-diMethylacetic Acid;4-[1-Oxo-4-[4-(hydroxydiphenylMethyl)-1-piperidinyl]butyl]-α,α-diMethylbenzeneacetic Acid;4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylphenylacetic acid;2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoic acid;Fexofenadine EP Impurity A
• CAS NO: 76811-98-8
• Molecular Formula: C₃₂H₃₇NO₄
• Molecular Weight: 499.647
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 76811-98-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 164-166 °C
• Boiling Point: 693.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.165
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility: Aqueous Acid (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Very Slig
• PKA: 4.16±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Fexofenadinone(CAS DataBase Reference)
• NIST Chemistry Reference: Fexofenadinone(76811-98-8)
• EPA Substance Registry System: Fexofenadinone(76811-98-8)

Safety Data

• Hazardous Substances Data: 76811-98-8(Hazardous Substances Data)

Usage

Uses

The oxo analogue of Fexofenadine (F322470); H1-histamine receptor antagonist and an active metabolite of Terfenadine (T114500).

Upstream product

• 154477-55-1 methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate 
• 70289-38-2 4-Chloro-1-(4-isopropyl-phenyl)-butan-1-one 
• 169280-04-0 1-[4-(1-Bromo-1-methyl-ethyl)-phenyl]-4-chloro-butan-1-one 
• 169280-21-1 2-[4-(4-chloro-butyryl)-phenyl]-2-methyl-propionic acid 
• 98-82-8 Isopropylbenzene 
• 1352802-40-4 methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)but-1-ynyl)phenyl)-2-methyl propionate oxalate 
• 154825-95-3 4-<4-<4-(Hydroxydiphenylmethyl)-1-piperidinyl>-1-butynyl>-α,α-dimethylbenzeneacetic acid methyl ester 
• 43076-30-8 4'-tert-butyl-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone 
• 76811-96-6 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid, ethyl ester hydrochloride 
• 832088-68-3 4-{[4-(4-hydroxydiphenylmethyl)-1-piperidinyl]-1-butynyl}-α,α-dimethylbenzene-acetic acid 

Downstream Products

• 83799-24-0 fexofenadine 
• 138452-21-8 fexofenadine hydrochloride 
• 847360-76-3 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-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.

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 THE PREPARATION OF KETO COMPOUNDS

A process for the preparation of 4-[1-oxo-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]butyl]-α,α-dimethylbenzeneacetic acid, useful as an intermediate for the preparation of fexofenadine, is provided.