Author Topic: Formation of tertiary amines in an Al/Hg reaction.  (Read 76 times)

Balkan Bonehead

  • Subordinate Wasp
  • ***
  • Posts: 117
Formation of tertiary amines in an Al/Hg reaction.
« on: June 23, 2010, 09:08:53 PM »
It is a well known process to reductively aminate a ketone with a primary amine to form a secondary amine with aluminum amalgam. An example would be MDP2P aminated with methylamine and reduced to form MDMA.

To what extent would the reaction of MDMA with MDP2P to form an quaternary imine, followed by reduction to the corresponding high m.w. tertiary amine, occur? It seems to me that this sidereaction would be minimized due to steric hindrance, but, of course, that is only conjecture.

lugh

  • Global Moderator
  • Foundress Queen
  • *****
  • Posts: 876
Re: Formation of tertiary amines in an Al/Hg reaction.
« Reply #1 on: June 25, 2010, 02:26:21 AM »
Not much according to the attached article on reductive amination  8)
Chemistry is our Covalent Bond

heisenberg

  • Dominant Queen
  • ****
  • Posts: 268
Re: Formation of tertiary amines in an Al/Hg reaction.
« Reply #2 on: June 26, 2010, 03:50:21 PM »
The intermediate wouldn't be too favorable considering it would have a + charge on the nitrogen, as well is being very hindered.
« Last Edit: June 26, 2010, 04:08:49 PM by heisenberg »
I spent all my money on booze and hookers, the rest I wasted - Charles Bukowski