The Vespiary

The Hive => Novel Discourse => Topic started by: Starblood on June 23, 2000, 07:37:00 PM

Title: 3,4 dimethoxy phenethyl alcohol as precursor?
Post by: Starblood on June 23, 2000, 07:37:00 PM

So are there any good methods for converting 3,4 dimethoxyphenethyl alcohol into good stuff?
I am thinking that the alcohol group would be a big pain to try to modify, any suggestions?

Title: Re: 3,4 dimethoxy phenethyl alcohol as precursor?
Post by: CHEM_GUY on June 23, 2000, 08:11:00 PM
I think that this would be a very good precursor.

You could slightly oxidize the alcohol into a aldehyde group and then go the Schriff Base route.

3,4-di MeO-C6H3-CH2-CH2OH  +  NaOCl dripped into an acidic medium -->  3,4-di MeO-C6H3-CH2-CH=O

3,4-Di MeO-C6H5-CH2-CH=O  +  NH2R  -->  3,4-Di MeO-C6H5-CH2-CH=NHR  --( H2)-->  3,4-Di MeO-C6H5-CH2-CH2NHR



This post is for informational purposes only an is not intended to facilitate illegal activity.
Title: Re: 3,4 dimethoxy phenethyl alcohol as precursor?
Post by: Rhodium on June 23, 2000, 08:51:00 PM
This would produce 3,4-dimetoxy-PEA. According to the text at my pharmacology page, this is only active in massive amounts or together with a MAOI.

http://rhodium.lycaeum.org (http://rhodium.lycaeum.org)

Title: Re: 3,4 dimethoxy phenethyl alcohol as precursor?
Post by: psyloxy on July 14, 2000, 07:35:00 PM
if one brominated this, would the Br be on the 2,5 or 6 ?

2 ... useless
5 ... Mescaline or Meta-Escaline
6 ... TMA-2


to make a PEA out of a PhEtOH :
1) R-OH --> R-Br with PBr3
2) R-Br to R-NH2 with NH3 or K-phtalimide


When going to the schiff base, does one use N-hydroxylamine and could one reduce it with NaBH4 to the amine or the hydroxylamine ??

But where would one find this precursor ?

--psyloxy--

Title: Re: 3,4 dimethoxy phenethyl alcohol as precursor?
Post by: Acme on July 15, 2000, 08:17:00 PM
Oxidize it to the acid; make the weinrab amide. Methyl grignard to the P2P, there you go.

Title: Re: 3,4 dimethoxy phenethyl alcohol as precursor?
Post by: psyloxy on July 16, 2000, 06:25:00 PM
Well, there are easier ways to get 3,4-diMeO-P2P but there's still intresting stuff to discuss.

I just had a look into several books but I couldn't find Weinrab mentioned anywhere so I guess a bit. Weinrab amide = ...dimethylamide ? Dimethylamides react with grignards to produce dimethylamine and a new carbonyl-compound. So if this is what we are talking about then why not use BzMgCl and N,N-dimethylacetamide to get P2P ?

--psyloxy--



Title: Re: 3,4 dimethoxy phenethyl alcohol as precursor?
Post by: Beaker on July 16, 2000, 10:03:00 PM
Would be brominated in the 5-position. At least, that's what happens with the related phenethylamine.

I just had a look into several books but I couldn't find Weinrab mentioned anywhere so I guess a bit. Weinrab amide = ...dimethylamide ?

WeinrEb amine = N,O-dimethylhydroxylamine. Condense with a suitable carboxylic acid derivative and you've got a WeinrEb amide.

Dimethylamides react with grignards to produce dimethylamine and a new carbonyl-compound.

This does not cleanly give ketones unless a huge excess of the amide is used, if at all. Thus, if the amide is the limiting reagent(as in this case), your yields would suck ass. With the Weinreb amide, low tempetature addition of a slight excess of the grignard or organolithium reagent usually gives a 80-95% yeild of the ketone.

So if this is what we are talking about then why not use BzMgCl and N,N-dimethylacetamide to get P2P ?

That's not what he was talking about.


Title: Re: 3,4 dimethoxy phenethyl alcohol as precursor?
Post by: psyloxy on July 16, 2000, 10:38:00 PM
Thanks for all the clarification!

So, even if it was not what we were talking about, BzMgCl and the Weinreb amide of AcOH would give P2P in good yield ?

--psyloxy--

Title: Re: 3,4 dimethoxy phenethyl alcohol as precursor?
Post by: Beaker on July 17, 2000, 09:16:00 AM
I don't know. Benzyl grignards are funny. They tend to give side products where they are alkylated at the position on the ring ortho to the -CH2-MgCl position.