Bwiti (PVC-Analog Taste-Tester)
07-30-02 07:01
No 338813
      Phenylcyclohexylamines Via Reductive Amination ?  Bookmark   

  If I sound completely off-base, that's because I've never taken a college chemistry course. How can reductive amination be applied to the production of phenylcyclohexylamines? I'm thinking that an Al/Hg can be done on phenylcyclohexanone/methylamine, or some other amine, but how's phenylcyclohexanone made? How about doing the same with cyclohexanone/phenylamine?....Wouldn't the end-product need to be rearranged? How would one go about synthing a benzaldehyde-like phenylcyclohexyl compound that can be reductively aminated with methylamine and sodium triacetoxyborohydride, or Al/Hg?cool

Love my country, fear my government.
(Chief Bee)
07-30-02 07:15
No 338818
      Reductive amination - no good  Bookmark   

Phenylcyclohexylamines are tertiary amines, therefore you cannot make them through reductive amination, as that reaction implies that you have a carbonyl compund to which you reductively add an amine. A carbonyl (double-bonded oxygen) on that center carbon would somehow require it to have five bonds (one to the benzene ring, two to the cyclohexane, and two to an oxygen), which it can not have, only four. 
(PVC-Analog Taste-Tester)
07-30-02 07:23
No 338825
      Thanks  Bookmark   

  Thanks! Well, that's one less thing that I'll be kicking around in my sick head, which will free up space for something

Love my country, fear my government.
(Hive Prodigy)
07-30-02 07:45
No 338842
      But  Bookmark   

Im sure you know that 1-phenyl-cyclohexyl-1-amine can be reductively alkylated with acetaldehyde or formaldehyde, to PCE or (PCM?) respectively. I have no refs for this other than the illustrations on Rhodium's site, but it should work dandy in theory, as it is all very simple known chemistry.

The problem is acquiring the phenyl-cyclohexylamine. Type that in TFSE and answer my old questions will ya? wink

(PVC-Analog Taste-Tester)
07-31-02 07:10
No 339244 has a lot of crude ...  Bookmark has a lot of crude methods for producing phenylcyclohexylamine..Of course, the azide route would be cool, but the universities in my area don't have the refs for it, so I gave up hope on that a long time ago.
  Beagle said something interesting a while back:

"Another interesting compound that I am unsure of is ACP, where allyl replaces phenyl. I thought that the original JMC paper (which I still haven't found) said that this was a dud, but there is animal data suggesting that it has 0.25 to 4.0x PCP's potency. Just replace allyl bromide for the bromobenzene and find out..."cool

Love my country, fear my government.
(Distinctive Doe)
08-03-02 21:53
No 340695
      well  Bookmark   

In some cases you can reductively aminate an alcohol

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