The Vespiary

The Hive => Newbee Forum => Topic started by: SMACK_WHORE on November 07, 2003, 04:23:00 PM

Title: stupid mofo question
Post by: SMACK_WHORE on November 07, 2003, 04:23:00 PM

if chlorine gas where passed through a solution of phenethylamine would it react with the benzene ring?

Title: Re: ""stupid mofo question"
Post by: java on November 07, 2003, 04:42:00 PM

No!,.......most likely make the salt and if  it's the base or else might react  with the Nh3 to NH2Cl in an acidic environment.....java

Title: FeCl3 cat Aromatic electrophilic substitution rxn
Post by: Relux on November 07, 2003, 10:56:00 PM

Feel free to correct me, but I don't think diatomic Cl would cause FB amines to be ionized.
   I think that passing Cl2 through this solution (solvent?), and forgive my regression to high school O chem, would do next to nothing but make you unhappy that your neighbors came over complaining that their house has suddenly been filled with nasty smelling pool fumes coming from that yellow gas emitting suspicious tube that is hanging out of your window.
On the other hand, if you were to mix this gassing with FeCl3, then you could possibly suspect that there would be some type of aromatic subsitution. Sorry, but this empty 40oz next to me provides that I do not know which position it would most likely react. I am only familiar with this rxn in a liquid reactant, so I don't know which solvent would be best (sorry). May we hear what might bee the sought result?

Title: Uhhhh.......Yeah....
Post by: TheCaterpillar on November 08, 2003, 05:44:00 PM

Title: the author (who follows laws obsessivly but likes
Post by: SMACK_WHORE on November 09, 2003, 08:40:00 AM

the author (who follows laws obsessivly but likes to theorize) was hoping to substitute the ring in 2 places...however upon more research i found the following:
aromatic compounds (like PEA) CAN be substituted in the presence of a halogen carrier and a halogen..however it only substitutes it one place(either the 2 or 4 position).
does anyone know anything about 2/4 methoxy PEA??

Title: Watch out!
Post by: Rhodium on November 11, 2003, 02:12:00 AM

Chlorine can react with the amine group of the phenethylamine, forming N-chloro-phenethylamine Hydrochloride - a toxic DNA alkylating agent.

Methoxyphenethylamines are inactive, UTFSE.

Title: Methoxyphenethylamines are inactive, UTFSE.
Post by: Capt_Stubing on November 11, 2003, 10:59:00 PM

Methoxyphenethylamines are inactive, UTFSE.

Hey Cheif I think ya ment to say "most" or "di-subsitated" there didn't ya? I don't want to belive that a guy like you could ever forget about mescaline! :)  ;)

Title: PEA's
Post by: Rhodium on November 12, 2003, 04:58:00 AM

I referred to mono-methoxy-PEA's (but as you brought up the subject, dimethoxies aren't active either).

When it comes to PEA's, it seems like a minimum of three substituents are necessary, and a maximum of four.

Title: Forget the gas,
Post by: ning on November 12, 2003, 08:33:00 AM

use a solid chlorinating agent, come on now...
TCCA in acetone or ethyl acetate or something should work much less stinkily for alkylations than chlorine gas.

Even bleach will do, if you adjust the ph correctly.

and rhodium, what about that infamous 2,6 dichloro mescaline?

Title: 2,6-Dichloromescaline
Post by: Rhodium on November 13, 2003, 07:34:00 AM

Yes, what about it? Hasn't various syntheses & trip reports been posted here over the years?

Here are a few related preparations:

2-Iodomescaline: J. Labelled Compd. Radiopharm. 41(1), 53-62 (1998)
2-Bromomescaline:

J. Org. Chem. 24, 917 (1959) (https://www.thevespiary.org/rhodium/Rhodium/pdf/2-bromomescaline.pdf)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/2-bromomescaline.pdf)
2,6-Dibromomescaline: Ber. 31, 1196 (1898)

2-Chloromescaline: Bioorg. Med. Chem. 10(11) 3555-3564 (2002)

Adapted from a very closely related compound:

To [Mescaline HCl] (0.1 mmol) in MeOH (3 mL) was added concentrated HCl (33 mL, 0.4 mmol). The solution was cooled to 0°C and a 90% aqueous solution of t-butyl hydroperoxide (44 mL, 0.4 mmol) was added. The resulting solution was refluxed overnight. Following cooling and removal of the solvent, the product (72%) was isolated by column chromatography.

Instead of the chromatography, an acid/base extraction, followed by gassing of the freebase with HCl and recrystallization (to remove unreacted Mescaline) can be used to purify the compound.

Title: just saying...
Post by: ning on November 14, 2003, 09:02:00 AM

that that one breaks the rule--all of its slots are full, right? 2,6 dichloro 3,4,5 trimethoxy phenylpropylamine ...
So I don't see why other compounds w/ >4 substituents couldn't work either, that's all...