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Author: Subject: N-Methylalanine digressions 2
WildAtHeart
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[*] posted on 14-1-2011 at 05:43
N-Methylalanine digressions 2


I am new to chemistry. I got a few couple questions. I am trying to make N-methyl-L-alanine. Uncle fester said to use Alanine. (sometimes i get the feeling he hadnt tried everything he wrote in his book) I got my hands on some L-alanine.

IS L-alanine WHAT I NEED?


The instructions i have posted below.

How important is the PH being 7?
Why Am I getting like 20 grams of crystals when uncle fester said it only makes 10 grams?
Can NaOH be used to neutralized the solution instead of baking soda?

1. Add 16 ml phosphoric acid to 200 ml water in a beaker.
2. Than add 9.5 grams of NaOH to form the monobasic sodium phosphate.
3. Now to this mixture add 10 grams alanine. Stir until it dissolves. The solution should be around 30 C.
4. Next add 10 ml 37% Formaldehyde, follow that with 15 grams zinc dust and stir for 45 minutes. Now let the zinc settle, then filter the almost clear water solution leaving the zinc on the bottom of the flask. It should filter clear water white through a couple of coffee tilters.

5. Now tor the important part, add baking soda powder slowly and with stirring until the PH reaches roughly 7. O let the water clear solution sit in the fridge overnight. Great heavy masses of long needle shaped N- methyl alanine will form. Let the mass grow to its greatest extent. Total yield is about 10 grams after the crystals have dried.







[Edited on 14-1-2011 by WildAtHeart]

[Edited on 14-1-2011 by WildAtHeart]
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starch
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[*] posted on 17-1-2011 at 20:36


new to chemistry ?

uncle fester ?

N-methyl-L-alanine ?

hmmmmmmmm not a good first post mate, 1 guess on what ur up to, it wont wash here





[Edited on 18-1-2011 by starch]

[Edited on 18-1-2011 by starch]
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[*] posted on 13-4-2011 at 18:32
alanine Vs N-methylalanine


What I cant understand is that on this site there is all this hype about reacting benzaldehyde with alanine?.....

If one wants to get the best results they should just make N-methylalanine and then react this with benzaldehyde and it will make a racemic mixture of ephedrine and pseudoephedrine. It works and has been proven in several articles.

Why are most people on this site using just alanine and not N-methylalanine???............................
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[*] posted on 13-4-2011 at 18:40
funny


Ha ha ha :)

it's like;

1
+
1
=

2?.....

Mmmmmmm lol

Quote: Originally posted by questions  
What I cant understand is that on this site there is all this hype about reacting benzaldehyde with alanine?.....

If one wants to get the best results they should just make N-methylalanine and then react this with benzaldehyde and it will make a racemic mixture of ephedrine and pseudoephedrine. It works and has been proven in several articles.

Why are most people on this site using just alanine and not N-methylalanine???............................
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azo
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[*] posted on 13-4-2011 at 19:39


Proberly because they want to make phenylpopanolamine and not ephedrine , I dont no how many times people have been told that you are better of forming the aldimine in methanol first, followed by the reduction to the amine with a metal hydride . the way you are trying to acheive this without over alkylating is not possable , I would hate to be the one trying to seperate the secondry amine from the tertiary amine . best of luck
Anyway if you had benzaldehyde why would you not procede to phenyl 2 nitropropene followed by reduction to amphetamine and then monomethylate to give racemic methamphetamine.

just another question

Is it as important to remove the water during the formation of the aldimine to drive the reaction towards imine formation as it is in the formation of the imine from a hemiaminol, and could somone provide some parametres for this reaction (ect) temperature , time and whether the aldimine is stable once isolated if possable . also any thoughts on the solubility , melting point , pkb of the aldimine



regards azo
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[*] posted on 13-4-2011 at 21:21


I made N-methylalanine the way fester said to and then I made the benzaldehdye and when I reacted them together the solution turned dark red. This was in October last year 2010, I'm not going to do these sorts of experiments anymore but it still gets me interested to disscuss the chemistry, it's facinating to me.
I then added an equal volume of toluene and extracted the product and I then applied an equal volume of Hcl (10%) to the toluene extract twice and combined these two extracts and then brought the ph of the combined solutions to 14.
As the PH started to move toward 14 I noticed more and more stuff falling to the bottom of the beaker. This has got to be the ephedrine and pseudoephedrine racemic mixture as there is no other explanation for it.........

Does anyone agree or dissagree?

However I forgot to blow steam into the acidic solution to rid all the benzaldehyde that was still present in the solution before I started to bring the ph up, and so therefore, when I tried to salt out the ephedrine and pseudoephedrine mixture by blowing dry Hcl gas into it, nothing precipitated.
I think it was because there was still benzaldehyde present as the combined acidic extracts were a brown colour before I brought thr PH up and so I'm thinking there was still benzaldehyde present

Does anyone know why I couldn't precipitate the ephedrine and pseudoephedrine mixture?

Cheers
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azo
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[*] posted on 13-4-2011 at 21:49


So you performed half an a/b extraction you should of washed the toluene extracts with just ph13 water first to remove any water soluable compounds (ect n methylalanine , then add more fresh water and ph with hcl to 7 then washed the water layer with toluene 2 or three times then basify to 13 and extract product into toluene for salting out .
I dont think it was ephedrine that presipitated as ephedrine freebase is soluable in water.and you said that it presipited when basified.

shorly some people have 2 bobs worth about alkylating amino acids
the way i discribed.or is eveyone sitting on the fence waiting to pounce.


regards azo
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[*] posted on 13-4-2011 at 23:23
wrong :(


AZO, you dissapoint me.
Ephedrine and pseudoephedrine freebase are not soluble in water with a ph significantly above 7.
The only time ephedrine and pseudoephedrine are soluble in water is when the ph is either 7 or lower, eg ephedrine Hcl or pseudoephedrine Hcl.
However it is not soluble with a low ph when in toluene, naptha or ether ect. But when the ph is high it dissolves beatifully in these liquids.

And I was actualy listening to your advice earlier :(

Don't worry.

Quote: Originally posted by azo  
So you performed half an a/b extraction you should of washed the toluene extracts with just ph13 water first to remove any water soluable compounds (ect n methylalanine , then add more fresh water and ph with hcl to 7 then washed the water layer with toluene 2 or three times then basify to 13 and extract product into toluene for salting out .
I dont think it was ephedrine that presipitated as ephedrine freebase is soluable in water.and you said that it presipited when basified.

shorly some people have 2 bobs worth about alkylating amino acids
the way i discribed.or is eveyone sitting on the fence waiting to pounce.


regards azo
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azo
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[*] posted on 14-4-2011 at 01:27


Ephedrine will disolve in basic water solution and not precipitate but will tranfer into a non polar layer if added ! unlike methylamphetamine
freebase which floats on the top of water.


regards azo
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[*] posted on 14-4-2011 at 02:41


silence thats the go ! good to see everyone jumping over themselves to help, maybe next time or maybe post again in another 5 years.
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[*] posted on 14-4-2011 at 10:34


Who told you such nonsense?



Knowledge is useless to useless people...

"I see a lot of patterns in our behavior as a nation that parallel a lot of other historical processes. The fall of Rome, the fall of Germany — the fall of the ruling country, the people who think they can do whatever they want without anybody else's consent. I've seen this story before."~Maynard James Keenan
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azo
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[*] posted on 14-4-2011 at 13:23


thats not nonsence its fact thats how much you no

[Edited on 14-4-2011 by azo]
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[*] posted on 14-4-2011 at 13:37


Yeh (ah..chem)your right... i don't know a thing I guess. What was I thinking. Stating that an oil will not dissolving in water..... I must need some sleep I guess.

But just in case see what happens when Ephedrine sulfate is added to a 5% NaOH solution. You should get a clear mixture since its soluble... right?




Knowledge is useless to useless people...

"I see a lot of patterns in our behavior as a nation that parallel a lot of other historical processes. The fall of Rome, the fall of Germany — the fall of the ruling country, the people who think they can do whatever they want without anybody else's consent. I've seen this story before."~Maynard James Keenan
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azo
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[*] posted on 14-4-2011 at 15:21


That's correct as long as the ph is 13 it will do what you said providing there is no non polar solvent used.

That is the benifit of a hydroxy group on the alpha carbon pitty some people want to remove it ! haaa sorry replace it

remember pseudoephedrine freebase is a powder.

regards azo:)

[Edited on 14-4-2011 by azo]
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[*] posted on 14-4-2011 at 23:51


well i suppose if i wanted my equestion answered i should have not mentioned that dirty word a,
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[*] posted on 15-4-2011 at 02:27


Has the use of pyridinium with pyridine occured or been mentioned by anyone yet?.

Being that pyridium is the cationic form of pyridine ( used in fre/crafts acylation's ) they should work together to donate an N and create a better leaving group for the (hopefully) now solid n-l-alanine product. All that is left would be to methyate it.

is this something that could work.

(I don't have a better understanding of chemistry, so if this is useless, I apologise now.) Xtal
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[*] posted on 15-4-2011 at 04:20


Making N-methylalanine is the easy part, its making the benzaldehyde that's the hard part.

Has anyone got a good benzaldehyde receipe?
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azo
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[*] posted on 15-4-2011 at 15:46


Hi questions have you done a melting point test to comfirm that it is n methylalanine . and did you isolate your sodium phospate or did you make it in situ.

i have made benzaldehyde before using benzyl alcohol and mn02 very easy to do but never got around to doing a seperation and distilation.


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[*] posted on 16-4-2011 at 00:29


Na I havent done any such tests on the n-methylalanine

The problem is making n-methylalanine is very temperamental and the yeilds are very low and it is a big job to make it and also takes much time.

It's not really worth it to be honest.

What about just reacting L-alanine with benzaldehyde, will that work and if so how temperamental is it?
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[*] posted on 16-4-2011 at 18:57


read the previous thread for your bonus answer.
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[*] posted on 17-4-2011 at 04:40


If ephedrine trough akabori is the goal, why not precipitate PPA*H3PO4 by adding excess phosphoric in acetone to the final extract, then try the Zn/Formaldehyde monomethylation? Work up with tartaric acid? Ya know :)
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[*] posted on 17-4-2011 at 06:31


This must be one of the dumbest discussions lately. It hurts my eyes to read this! At first I thought to just split it of the Akabori reaction thread and move to Beginnings, but then I saw this is the second such series of posts that recently managed to degrade both threads on the Akabori reaction. If one warning was not enough, then I'm sure two will not do either. So Detritus it goes.
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