Flouxetine

[Chromatograph]

Flouxetine(prozac) has an ether complex on a 2ndary benzyl C. could an S_n1 substitution (Nu:- would probably be NaOH?) yield a phenylmethylamine or can strictly benzyl halides undergo S_n1 on a 2ndary C?
What do you do with a dead chemist?
    ...Barium

[Rhodium]

Ethers does not undergo substitution reaction with amines, if that's what you are asking. It's spelled Fluoxetine, by the way.

[Chromatograph]

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 (S_n1) 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

[Rhodium]

Catalytic hydrogenation should be able to create Ph-(CH₂)3NHCH₃ and trifluoromethylphenol, but I can't think of anything else.