January 26, 2023

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Hello so today we are going to discuss synthesis of fluoxetine so basically fluoxetine is what it is non tricyclic antidepressants right we have seen that there is one category that is tc that is tricyclic antidepressants and the another one is non-tricyclic antidepressant so where it is non-tricyclic antidepressant it means that there is a lack of fused tricyclic

System so basically floccitine is uh synthesized from the reactant that is acetophenone now this acetophenone undergoes manic reactions in presence of formaldehyde so that will produce is the structure one so here you can correlate that acetophenone undergoes manic reaction in presence of uh formaldehyde so that will give us uh formaldehyde and dimethylamine so

That will give us this structure one so it is expected that this ch2 is coming from the formaldehyde and this multi is coming from the dimethyl amine so basically manic reaction involves the uh addition of acetophenone formaldehyde and dimethylamine so that all leads to the reaction uh that is called as manic reaction and gives structure one so this structure one

Then undergoes reduction because in the structure we are observing that carbonyl group is present so this carbonyl group undergoes reduction so here there is a conversion of ketone into alcohol because reduction is what simple addition of hydrogen so here that carbonyl group is present that will undergoes or that ketone is uh converted into alcohol by reducing

Agent now once we are getting that oh moiety in structure 2 that will be acted upon by chlorinating agent so that chlorination can be done by pcl3 pcl5 or socl2 so specifically that structure 2 is acted upon by this chemical socl2 so here that oh is converted or replaced by cl so we are getting here chlorinated compound so structure 2 undergoes chlorination that

Will give the structure 3 now this structure 3 is acted upon by the structure or the chemical that is trifluorocarbon uh phenol or paratrifluorocarbon or para trifluoromethyl phenol so here that is uh the reaction because this this we need as a side product in the structure of fluxity so now here main parent chain we have prepared now we have to incorporate the

Side chain so now here there is a addition of this trifluoromethyl phenol into the structure three so we are getting this structure for so it is expected that this o h moiety that is going to attack here right and this will get eliminated so ultimately by the loss of hcl there is a introduction of this trifluoromethyl phenoxy moiety to this parent chain so first

What we have done we have first synthesized the parent chain by the managed reaction and reduction and then ultimately we have incorporated the side chain that is trifluoromethyl phenoxy substituent and ultimately then structure four we are getting that is acted upon by this uh cyanide bromocyanide as well as potassium hydroxide so here that is simply the end

The alkylation so this bond will get break down so we are getting here only monomethyl moiety right so that undergoes nd alkylation or nd methylation so we are getting monomethyl multi so this is the structure of phlox setting so for fluoxetine first we have synthesized this parent moiety this parent chain then we have introduced this side chain right and then

Just nd alkylation or antimethylation so which will leads to the final compound that is floxity so basically fluoxetine is what it is non tricyclic antidepressant so acetophenone undergoes manic reaction that will produce a structure one so there is reduction of this ketonic group into alcohol moiety then there is a chlorination and then there is addition of side

Chain that is trifluoromethyl phenol and then ultimately there is nd methylation so we are getting fluoxetine as the final product

Transcribed from video
fluoxetine synthesis By ChemEase