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Wellcome To My Presentation Topics: Synthesis of Fexofenadine

This document presents a synthesis route for fexofenadine involving 8 steps. Fexofenadine is an antihistamine drug that acts as a selective peripheral H1-blocker. The synthesis begins with benzene and methallyl alcohol acetate in a Friedel-Crafts alkylation reaction. It proceeds through steps of hydrolysis, oxidation, esterification, and reduction to obtain intermediates. The final step is an alkaline hydrolysis to yield the target molecule, fexofenadine. Diagrams illustrate each step in the multi-step synthesis process.

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Mohammad Nuruzzaman
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202 views11 pages

Wellcome To My Presentation Topics: Synthesis of Fexofenadine

This document presents a synthesis route for fexofenadine involving 8 steps. Fexofenadine is an antihistamine drug that acts as a selective peripheral H1-blocker. The synthesis begins with benzene and methallyl alcohol acetate in a Friedel-Crafts alkylation reaction. It proceeds through steps of hydrolysis, oxidation, esterification, and reduction to obtain intermediates. The final step is an alkaline hydrolysis to yield the target molecule, fexofenadine. Diagrams illustrate each step in the multi-step synthesis process.

Uploaded by

Mohammad Nuruzzaman
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PPT, PDF, TXT or read online on Scribd
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Wellcome to My Presentation

Topics: Synthesis of
Fexofenadine
Md. Nuruzzaman
Roll NO. :13055085
M.Sc. Engineering 1st Semester
Dept. of Applied Chemistry & Chemical
Engineering
University of Rajshahi
Fexofenadine
Fexofenadine is an antihistamine pharmaceutical drug used in the treatment of
allergy. Therapeutically, fexofenadine is a selective peripheral H1-blocker. The
chemical name of fexofenadine is 4-{4-[4-(hydroxyl biphenyl methyl)-1-
Pepperdine]- 1-butyl hydroxyl acryl}-a,a-dimethyl phenyl acetic acid, with
molecular formula C32H39NO4 and molecular weight 501. It’s structural formula is
given below.

Fig. Structure of fexofenadine.


Synthesis of Fexofenadine
There are many fexofenadine synthesis routes ,according to W. Ronggeng et al,2013 for the
synthesis of fexofenadin benzene and methallyl are used as starting reactants, applying steps
of Friedel–Crafts alkylation reaction, hydrolysis, oxidation, esterification reaction, and
reduction reaction to obtain the intermediate product, followed by N-alkylation reaction to
obtain 4-{1-hydroxy-4-[4-(hydroxydiphenyl)- piperidine]butyl}-a,a-dimethylbenzene
acetate. Then, the final product fexofenadine is obtained upon hydrolysis. 8 steps are
involved in the synthesis of fexofendine according to this method;
1. In the first step benzene is acetated by methyl ally alcohol acetate to get α,α-dimethyl
phenyl propyl alcohol acetates.

methallyl

α,α-dimethyl phenyl propyl alcohol


benzene
acetates
Synthesis of Fexofenadine…
2. In the 2nd step α,α-dimethyl phenyl propyl alcohol acetates react with 4-butyl chloride to
get 2-[4-(4-butyric chloride)-phenyl]-2-methyl propyl acetate.

+ 4-butyl chloride

2-[4-(4-butyric chloride)-phenyl]-
2-methyl propyl acetate
Synthesis of Fexofenadine…
3. In the 3rd step, by alkaline hydrolysis we get 2-(4-cyclopropyl carbonyl)-phenyl-2-
methyl propel alcohol.

Alkaline
hydrolysis

2-(4-cyclopropyl carbonyl)-phenyl-
2-methyl propel alcohol
Synthesis of Fexofenadine…
4. In the 4th step oxidation of the alcohol to acids by potassium permanganate to get
2-(4-cyclopropyl carbonyl)-phenyl-2-methyl propionate acid.

oxidation

KMnO4

2-(4-cyclopropyl carbonyl)-
phenyl-2-methyl propionate acid
Synthesis of Fexofenadine…
5. In the 5th step esterification takes place by adding ethanol in acidic condition, as a
result 4-(4-chloral-1-carbonyl-butyl)-α,α-dimethyl phenyl acid ethyl ester is obtained.

Esterification

C2H5OH

4-(4-chloral-1-carbonyl-butyl)-
α,α-dimethyl phenyl acid ethyl
ester
Synthesis of Fexofenadine…
6. In the 6th step, the carbonyl is reduced to hydroxyl by sodium borohydride to get
4-(4-chloro-1-hydroxyl-butyl)-α,α-dimethyl-ethyl phenyl acetate.

Reduction

NaBH4

4-(4-chloro-1-hydroxyl-butyl)-
α,α-dimethyl-ethyl phenyl
acetate
Synthesis of Fexofenadine…
7. In the 7th step, reaction with α, α-diphenyl-4-piperidine methanol obtains 4-{1-
hydroxyl-4-[4-(hydroxyl biphenyl methyl)-1-piperidyl]butyl}-α,α-dimethyl phenyl
acetic acid ethyl ester.

α, α-diphenyl-4-
piperidine methanol

4-{1-hydroxyl-4-[4-(hydroxyl biphenyl
methyl)-1-piperidyl]butyl}-α,α-dimethyl
phenyl acetic acid ethyl ester
Synthesis of Fexofenadine…
8. Finally, the final product fexofenadine is obtained after Alkaline hydrolysis.

Alkaline
hydrolysis

Fexofenadin
THANK YOU

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