12-18-02 23:22
No 390589
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
(Chief Bee)
12-18-02 23:28
No 390590
Ethers does not undergo substitution reaction with amines, if that's what you are asking. It's spelled Fluoxetine, by the way.
(Stranger)
12-18-02 23:58
No 390599
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
(Chief Bee)
12-19-02 02:02
No 390642
Catalytic hydrogenation should be able to create Ph-(CH2)3NHCH3 and trifluoromethylphenol, but I can't think of anything else.