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The Hive => Chemistry Discourse => Topic started by: Chromatograph on December 18, 2002, 11:22:00 PM

Title: Flouxetine
Post by: Chromatograph on December 18, 2002, 11:22:00 PM
Flouxetine(prozac) has an ether complex on a 2ndary benzyl C. could an Sn1 substitution (Nu:- would probably be NaOH?) yield a phenylmethylamine or can strictly benzyl halides undergo Sn1 on a 2ndary C?
What do you do with a dead chemist?
    ...Barium
Title: SN
Post by: Rhodium on December 18, 2002, 11:28:00 PM
Ethers does not undergo substitution reaction with amines, if that's what you are asking. It's spelled Fluoxetine, by the way.
Title: oops
Post by: Chromatograph on December 18, 2002, 11:58:00 PM
oops. thats not what i meant. heres a more understandable form of my question. could fluoxetine undergo substitution with something like OH- as the attacking nucleophile at this site(*):
            Ph
             |
 F3C-PhO-CH*-(CH2)2NHCH3
to yield:
     Ph       
     |    
Nu-CH(CH2)2NHCH3
(Nu is the incoming nucleophile)
As it is a benzylic carbon, i figure that site would readily undergo first order nucleophilic substitution (Sn1) with a stongly basic nucleophile. although i have a feeling that that only occurs with halogenated benzyls, at least on 2nd degree carbons. what do you think?
does anyone know or can think of any other pathways to this or a similar product from fluoxetine?
What do you do with a dead chemist?
    ...Barium
Title: Catalytic hydrogenation should be able to create ...
Post by: Rhodium on December 19, 2002, 02:02:00 AM
Catalytic hydrogenation should be able to create Ph-(CH2)3NHCH3 and trifluoromethylphenol, but I can't think of anything else.