Author Topic: Alkylation of amines (Read 3163 times)

periannath · « **on:** March 15, 2003, 08:48:00 PM »

(I was going to post this to the tryptamine forum but since this could be applicable to any amine I decided to post here.)
Say I had just reduced melatonin to 5-MeO-NET with LiAlH₄ or whatever and reacted it with an excess of methyl iodide to form the quaternary ammonium salt 5-Methoxy dimethylethyltrypammonium iodide. I would get a mixture of 5-MeO-DMT and 5-MeO-MET when I dequat. Correct?

periannath · « **Reply #1 on:** March 16, 2003, 05:53:00 PM »

All I need is a simple yes or no. If no I would appreciate a reason.

Rhodium · « **Reply #2 on:** March 17, 2003, 04:02:00 PM »

You will likely get almost exclusively 5-MeO-MET, as methyl groups are removed preferentially in most dequaternization reactions.

periannath · « **Reply #3 on:** March 17, 2003, 04:35:00 PM »

Thanks! That was the answer I was hoping for. However I now realize It might be easier methylated with formaldehyde.

Rhodium · « **Reply #4 on:** March 18, 2003, 03:33:00 PM »

If you UTFSE you will see that not many formaldehyde methylations are tryptamine-friendly (NaBH3CN being an exception).

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Author Topic: Alkylation of amines (Read 3163 times)

periannath

Alkylation of amines

periannath

Is there anybody out there.

Rhodium

You will likely get almost exclusively ...

periannath

Thanks

Rhodium

Tryptamine methylation