ko3 synthesis from DOI

[ChuangTzu]

Some of you might remember a post I made a while ago entitled Mathematical Hallucinogens. The post was supposed to be a summary of an article on possible novel hallucinogens discovered by QSAR methods[1] but I never had time to make the promised updates (sorry: ) and so the only one I got around to talking about was ko3:

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I'd like to hear what you all think about possible ways of hypothetically attacking the synthesis of this stuff using DOI as a starting material. I don't mean to write out a full procedure; something like "Hmm, I wonder if you could cook it up with X, distill off the Y, and then reduce over Z" is what I'm looking for.

On a side note, I'm taking a course right now for which I'm going to be plugging ko3 into a different QSAR scheme in an attempt to cross-validate the results of Shulze-Alexandru's study.

Thanks for the input =).

[1]Shulze-Alexandru et al., Quant. Struct.-Act. Relat., 18 (1999)

 

[BilZ0r]

Id stick with the DOI personallly... thats a nice chem. I mean, if you end up with something to much more potent, how the fuck are you gonna weight it out?

 

[sorceror]

hmmm starting with DOI might be a bit too hard - alkylation of primary amines isnt a clean reaction, youll be getting too many side products...

this is out of my scope of knowledge, but id guess a good way to do it might be reductively aminating (2,5-dimethoxy-4-iodophenyl)propan-2-one with 3-amino-N,N-diethylpropanamide

removing the -NH2 group and replacing it with an oxygen in order to get from DOI to (2,5-dimethoxy-4-iodophenyl)propan-2-one is beyond me

good luck eh, be safe.

 

[Mr.C6H6]

As I mentioned in the original thread, this is very simple to make: 3-chloropropanoylchloirde is reacted with Et2N, and the product then with DOI.

 

[sorceror]

^ wont reacting the haloamide product with DOI cause too much substitution at the DOI nitrogen, giving a very low yield and forming tertiary amine and quarternary ammonium salt side products?