Enamine Formation/Reduction
Since this post has no references I would hope that it is obvious that I am merely intending to draw upon the knowledge of those of you with many
years of practical laboratory experience. I have searched the literature and internet to a great degree and learned much already. I soon intent to
take a quantity (around 25g) of alpha-phenylacetophenone (deoxybenzoin) and condense it with a secondary amine, 1-phenylpiperazine, to form the
enamine thereof. Obviously after wards I am going to reduce the enamine to a saturated amine with sodium borohydride. I have several ideas and have
read several suggested procedures with various reaction solvents and catalysts. However before I attempt the procedure I thought I'd ask anyone with
any ACTUAL experience with this type of enamine reduction to throw in their two cents. Whether it's solvent type, catalyst or catalyst amount, in situ
enamine formation followed by reduction versus isolating the enamine first and then reducing it to a saturated amine, etc etc.
Thanks for any and all input and I'll be sure to let you know the methods and results after workup is complete. By the way in case anyone was curious
the alpha-phenylacetophenone was prepared from Acetophenone, K t-Butoxide and Iodobenzene, in DMSO as discussed (briefly) in my previous thread
entitled "Haloalkane Synthesis Help".
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