Yet another phenylalanine post- SMACK-WHORE

java · Consumer

SMACK_WHORE
(Stranger)
10-05-03 10:36
No 462732




yet another phenylalanine post
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ok is this feasable?i cant be arsd balancing and obviously anhydrous is needed all the way especially in step no.2....

1) phenylalanine+Cl2+U.V+Heat --->Benzene-CH2-(CO2H-CCl-NH2)+HCl
2)Benzene-CH2-(CO2H-CCl-NH2)+CH3OH -->
Benzene-CH2-(CO2H-COCH3-NH2)
3)Benzene-CH2-(CO2H-COCH3-NH2)+NaOH+heat -->
Benzene-CH2-(CH2OCH3)-NH2+Na2CO3 A.K.A. Alpha Methoxy Phenethyl Amine

Ok its No amphetamine but whats an extra Oxygen atom??i havent found anything relating to the activity of this compound.
PS this is Alpha methoxy PEA ie the carbon atom next to the nitrogen bears the methoxy group NOT the Carbon atom next to the benzene ring
I know this seems like a crappy synth to a crappy substance but never mind!

Kurt Kobains dead....NEVERMIND!

Rhodium
(Chief Bee)
10-05-03 11:35
No 462738




Chlorine/UV/Heat = Molecule Hell
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Phenylalanine + Cl2 + U.V. + Heat

That sounds like an excellent way of polymerizing the entire molecule, or at least destroying the amine... Where did you get that idea?

Besides, have you completely missed Post 309268 (Rhodium: "---- related posts go in the STIMULANTS forum!", Newbee Forum)

SMACK_WHORE
(Stranger)
10-05-03 12:10
No 462743




modern Organic chemistry (R.O.C. Norman D.J. W.)
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i got the idea from the thory that a C-H bond next to the Carbonyl of a carboxylic acid can be turned into a C-Cl bond in the presence of U.V light and heat.
if the amines in danger how about the HCl salt(is that possible with an amino acid?
obviously the whole procedure would require alot of control in respect to PH and the like

"if i had a nickel for every penny id have a lottle o quaters!"-george turnbog ( Surprised

)

Rhodium
(Chief Bee)
10-05-03 12:33
No 462750




Synthesis of Phenylalaninol Methyl Ether
(Rated as: excellent)
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I had a look, and there are no literature references available about the pharmacological effects of Phenylalaninol Methyl Ether (amphetamine with a methoxy group on its alpha-methyl group). However, below follows a synthesis of it:

Synthesis of alpha-methoxymethyl-phenethylamine (Phenylalaninol methyl ether)
J. Org. Chern., 43(5), 892-898 (1978)

Phenylalanine -> Phenylalaninol -> Phenylalaninol Methyl Ether

(S)-(-)-Phenylalaninol

This was prepared according to the method of Yamada[14] mp 88-90?C, [a]25D -25.4? (c 1.22, EtOH). Alternatively, it was prepared by the procedure of Brown's[15] and that of Lane[16] and all three methods gave similar results. The latter method[16], in our hands, proved to be the most convenient.

(S)-(-)-2-Amino-1-methoxy-3-phenylpropane

A solution of 18.4 g (0.122 mol) of (R)-(-)-phenylalaninol in 250 mL of anhydrous tetrahydrofuran was added dropwise to a stirred suspension of 5.23 g (0.130 mol) of potassium hydride (pentane washed) in 100 mL of tetrahydrofuran at 25?C under nitrogen. The resulting pale yellow gelatinous mixture was allowed to stand overnight and then a solution of 17.0g (0.119 mol) of methyl iodide in 150 mL of THF was added dropwise over 2 h. Mixing was accomplished by external shaking, since the gelatinous mixture would not stir with magnetic stirring bars. The reaction components were allowed to mix an additional 3 hand then poured into 1 L of cold saturated brine, extracted with ether (3x), dried with Na2SO4, and concentrated to give 24.9g of crude product. Distillation gave 17.1g (bp 55-59?C/0.1mmHg) of a clear oil which on standing became cloudy and rapidly produced a white precipitate which was found to be the carbonate. It was subsequently found that conversion of the freshly distilled methoxyamine to its hydrochloride salt was a more convenient way to store the compound. Thus the methoxyamine (17.0g), immediately after distillation, was dissolved in 700 mL of absolute ethanol and dry HCl bubbled in for 10 min. The resulting solution was concentrated, in vacuo, to furnish 20.5g of a colorless solid which was recrystallized from ethanol-ether (13:1), mp 151-152?C.

To release the free methoxyamine, it was dissolved in 5% potassium carbonate solution and extracted with ether, dried (Na2SO4), and concentrated. Bulb-to-bulb distillation (bp 52?C/0.1mmHg) gave the product as a clear oil.

References
[14] H. Seki, K. Koga, H. Matsuo. S. Ohki, I. Matsuo, and S. Yamada, Chem. Pharm. Bull., 13, 995 (1965).
[15] N. M. Yoon, C. S. Pak. H. C. Brown, S. Krishnamurthy, and T. P. Stocky, J. Org. Chem., 38, 2786 (1973).
[16] C. F. Lane (Aldrich-Boranes, inc.), Patent US3935280

SMACK_WHORE
(Newbee)
10-08-03 01:46
No 463332




that isnt the compound im talkin bout ...
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that isnt the compound im talkin bout though....the one im talkin about is just plain old methoxy stuck onto that alpha carbon.just like Phenylalaninol Methyl Ether but minus a carbon....sorry if im not been clear i cant use mark up so i cant put a pic of it up..... Sad

"if i had a nickel for every penny id have a lottle o quaters!"-george turnbog ( Surprised

)

Rhodium
(Chief Bee)
10-18-03 20:00
No 465515




Posting molecular images
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Taken from Post 305766 (Rhodium: "FAQ, Tips & Tricks", General Discourse)

Q: How do I post molecular images? How can I generate SMILES code? What formats can I use?

A: See Post 305167 (Rhodium: "Hive Molecular Structure Drawing Applet", General Discourse). In that thread you will also find links to the SMILES FAQ and programs capable of generating such code. For information about valid file formats, see Post 305273 (Lilienthal: "advanced features...", General Discourse).

SMACK_WHORE
(Newbee)
10-28-03 15:28
No 467376




BEHOLD!
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alpha methoxy phenethylamine in all its LEGAL glory:

____    NH2
   //   \\ /C\ /
//    \\/ \ /
\    / C
   \    /    |
===    OCH3

"if i had a nickel for every penny id have a lottle o quaters!"-george turnbog ( Surprised

)

Blind_Angel
(Hive Bee)
10-28-03 21:26
No 467425




what the difference between this one and the...
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what the difference between this one and the one Rhodi posted

/}/_//\//) /-|/\//¨/=/_

SMACK_WHORE
(Newbee)
10-29-03 07:48
No 467515




why wont ppl see??????
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just fuckin look at it!!!!!the one rhodium posted has C-OCH3
attached to the alpha carbon..the one i drew has just OCH3 attached to the alpha carbon..its a subtle 1 carbon difference but it is a difference!!!!!!!

"if i had a nickel for every penny id have a lottle o quaters!"-george turnbog ( Surprised

)

Rhodium
(Chief Bee)
10-29-03 08:05
No 467525




Not a good amphetamine analog.
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Alpha-methoxy-amines are sensitive to hydrolysis and tend to form the corresponding imine and methanol in aqueous solutions.

SMACK_WHORE
(Newbee)
10-29-03 14:38
No 467629




what about?
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what about N-methyl- phenyethylamine?

"if i had a nickel for every penny id have a lottle o quaters!"-george turnbog ( Surprised

)

Rhodium
(Chief Bee)
10-29-03 17:14
No 467681




stable, but inactive
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That is stable, but devoid of all activity in humans up to several hundred milligrams.

SMACK_WHORE
(Newbee)
11-05-03 13:06
No 468961




ok but what about....
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does this idea sound better?making an ester of phenylalanine then reducing this via a primary alcohol and lithium metal to make phenylalinol and a primary alcohol...
i know many bees would find a usefull purpose for phenylalinol..any comments on this????

"if i had a nickel for every penny id have a lottle o quaters!"-george turnbog ( Surprised

)

Rhodium
(Chief Bee)
11-05-03 13:22
No 468963




Provide references for that Li reduction
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That doesn't sound like a usable route to me... Too low selectivity and yield.

SMACK_WHORE
(Newbee)
11-05-03 14:09
No 468967




no reference
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i dont have a reference..the idea came from the basic Na/ethanol reduction of esters to alcohols..i just presumed Li can be used in place of sodium as it still has an s orbital just a 3S instead of 2S..my thoughts where it would just be a lot slower..
i was more concerned about making the ester..which side would the equilibrium lie to, and how concentrated would the acid catylyst need to be?and which part is too unselective, i cant see any unselective bits

"if i had a nickel for every penny id have a lottle o quaters!"-george turnbog ( Surprised

)