DMT via enamine reaction, possible...?

[pHarmacist]

This is a result of my wild imagination rather than something serious, but could it work?

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[pH]armacist - Never underestimate the power of retrosynthesis. Svenskar suger på fotboll!

[Cyrax]

The Stork enamine alkylation is a good idea, however I don't see how you can easily go from the ketone to the indole ring.  Probably you need to reduce it first and then subject the alcohol to a beta-elimination.

The synthesis is a bit elaborate, but I don't see why the hell it shouldn't be possible.  It looks OK, mechanistically speaking.

Glad to see you like retrosynthesis (it rules).  Now, the following step would be: look up the reactions in the chemical literature to obtain lab procedures.  If the yield are OK, your synthetic scheme would be great.

Keep up the good work   .

[Lilienthal]

Nice idea. The last reaction can be accomplished with LiAlH4. But there might be a few problems:

- The first compound is not a ketone, it's an amide (or better: an anilide), so the first reaction might not work as expected.

- The second compound is not an enamine and will probably not react like one, it's an amino substituted aromatic ring similar to aniline.

- The product of the alkylation reaction will probably aromatize immediately, leaving you with a 2-pyrrolidyl-tryptamine.

[Cyrax]

The synthesis is a bit elaborate, but I don't see why the hell it shouldn't be possible.  It looks OK, mechanistically speaking.

Damned, I 'm a bit ashamed here ... I completely overlooked the amide (stupid me ...).  Yup, amides definitely don't react like ketones (resonance) ... so it won't work ...  

[pHarmacist]

Lilienthal: Of course, i didn't give it much thought, not at much all, it seemed ok then, but of course indolic nitrogen has a free e-par ... something I often miss when it comes to indolum .. well I guess I'll have to dust myself off and try agin.. my bad thank you for remarks guys..
[pH]armacist - Never underestimate the power of retrosynthesis. Svenskar suger på fotboll!