May 11, 2021, 07:32:10 PM
Forum Rules: Read This Before Posting


Topic: Amine `cleavage' can it be done?  (Read 265 times)

0 Members and 1 Guest are viewing this topic.

Offline Monoamine

  • Regular Member
  • ***
  • Posts: 18
  • Mole Snacks: +0/-0
Amine `cleavage' can it be done?
« on: March 15, 2021, 02:10:57 AM »
Hi there, I have a secondary amine in a cyclic structure and I need to install a carbonyl next to the amine. My though was to `cleave' the amine (in analogy with cleaving an ether), install a acyl halide group on one end, and fuse the two together again.

My main problem is that I can't find any references on how to cleave amines, although I'm sure its possible.

I apologize if this is something super basic that I should already know, but I've been stuck with this for quite some time and would be very grateful for any hints.

Thanks

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 1346
  • Mole Snacks: +91/-7
Re: Amine `cleavage' can it be done?
« Reply #1 on: March 15, 2021, 07:45:22 AM »
I have clevad amines with bromine. What you want to do does not  sound basic or simple, my guess is that it would be easier to install the carbonyl from the start, not incorporate it afterwords like you suggest. Can you post the structure?

Offline Monoamine

  • Regular Member
  • ***
  • Posts: 18
  • Mole Snacks: +0/-0
Re: Amine `cleavage' can it be done?
« Reply #2 on: March 22, 2021, 04:16:03 AM »
One additional difficulty is that the cleavage will probably happen at the more substituted carbon...

So maybe I'm better off just cleaving the  ether too, and then reform the ring with the amide...

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 1346
  • Mole Snacks: +91/-7
Re: Amine `cleavage' can it be done?
« Reply #3 on: March 22, 2021, 05:22:15 AM »
It just feel so much simpler to make the amide-ring from start, what you suggest here is very difficult. You can make a substructure-reaction search in Reaxys or Scifinder.

Sponsored Links