Author Topic: 1-(1-Phenylcyclohexyl)-4-phenylpiperidine  (Read 6144 times)

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« on: April 09, 2003, 08:05:00 AM »
Check this out:

1-(1-Phenylcyclohexyl)-4-phenylpiperidine (compound #13)
1-(4-Phenylpiperidino)cyclohexanecarbonitrile (12) was prepared from 24.5g (0.152 mol) of 4-phenylpiperidine and 18.7g (0.15 mol) of cyclohexanone cyanohydrin by refluxing azeotropically in 60ml of benzene for 3h. The residue was recrystallized from methanol-ethyl acetate (1:1), mp 106-107*C. A solution of 12g (0.044 mol) of 12 in 50ml of benzene was added dropwise to PhMgBr (from 2.0g of Mg and 12.5g of bromobenzene in 20ml of ether). The mixture was decomposed after 2h of reflux, blah, blah….
J. Med. Chem. 1981, 24, 499-502
  The article lists the above product (13) as one of three compounds which have analgesic properties rather than being like PCP (dissociative). I loathe seeing "cyclohexanone cyanohydrin", because I probably need fucking NaCN to make it, and just buying that cyano compound might arouse the suspicion of those filthy scum-bags at the DEA. Am I over-reacting? What if I just refluxed the 4-phenylpiperidine/cyclohexanone until it's dry, then add it to phenyl-lithium? Or, maybe make the tosylate salt and add it to PhMgBr?
  Anyway, I just thought that some of you might be interested.. I'm off to look for a synth of 4-phenylpiperidine.. Hmmmm, maybe phenylbutylamine could be used the create a compound that retains activity? Peace! 8)