The Vespiary

The Hive => Chemistry Discourse => Topic started by: mysterious on February 26, 2003, 04:53:00 AM

Title: proscaline
Post by: mysterious on February 26, 2003, 04:53:00 AM
hi all friends!!

anyone every tried proscaline (p)?? i read of it in shulgins book!! do you know if this substance can be made of any uncontrolled substances??

anyone who tried it: how would  you describe the effects??

nice greetings!!
mysterious
Title: Route
Post by: Barium on February 26, 2003, 05:46:00 AM
Syringaldehyde is alkylated with propyl iodide to 3,5-dimethoxy-4-propoxybenzaldehyde, the benzaldehyde is reacted with a chloroacetic acid ester in a Darzens condensation to give (3,5-dimethoxy-4-propoxyphenyl)acetaldehyde. This acetaldehyde can be reductively aminated with ammonia and Raney nickel, or the aldoxime formed with hydroxylamine which is then reduced to the amine proscaline (3,5-dimethoxy-4-propoxyphenethylamine). All reagents here are pretty unwatched.

Title: syringaldehyde from vanillin
Post by: Rhodium on February 26, 2003, 04:05:00 PM
And syringaldehyde is easily made from vanillin:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/mmda.mescaline.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/mmda.mescaline.html)

Title: Questions, questions.
Post by: Antoncho on February 26, 2003, 10:14:00 PM
the benzaldehyde is reacted with a chloroacetic acid ester in a Darzens condensation to give (3,5-dimethoxy-4-propoxyphenyl)acetaldehyde. This acetaldehyde can be reductively aminated with ammonia and Raney nickel

Mmmmm, can you elaborate on that? Ever done this? I mean, you once wrote you were going to, but thus far all i read from you was on P2Ps via chloropropionates. Maybee, i should UTFSE better?

I always had a notion of this method as of somehow untrustworthy since those acetaldehydes would bee very hard to keep from polymerisation.... no?


Antoncho
Title: Reductive amination of phenylacetaldehydes
Post by: Rhodium on February 26, 2003, 10:33:00 PM
See

Patent US5057624 (http://l2.espacenet.com/dips/viewer?PN=US5057624&CY=gb&LG=en&DB=EPD)

.
Title: easy is relative
Post by: hypo on February 27, 2003, 12:53:00 AM
> And syringaldehyde is easily made from vanillin:

iirc some bees (antoncho?) have had problems with the
methoxylation step.

uemura had big problems separating OH-vanillin from vanillin.
(ok, that's not syringaldehyde, but related)

i don't consider those syntheses "easy".
(for otc-bees. now if you have high grade chemicals it's probably a breeze...)