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Author Topic: Route to Amphetamine  (Read 296 times)

thecriscoking

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Route to Amphetamine
« on: July 09, 2012, 02:05:43 AM »
Hello everyone, this will be my very first post on thevespiary.org.

During looking over some notes today concerning Friedel-crafts reactions, I thought about an alternative route to amphetamine.  I did a BIT of research and did not find much on the synthesis (though it is very likely I have overlooked many things).  This should by no means be taken seriously until being looked over and discussed by those who have the knowledge, let this be just me thinking out loud and I would love to hear some input on the subject.

The synthesis seems pretty straight foreword (if correct) and I don't see how any of the reactants should be dangerous or watched, so here it goes:
(I apologize in advanced for my beginner chemdraw skills)



A couple concerns regarding the second step of the reaction (the addition of H2O); I am not 100% sure that the Iodide near the Chloride would detach and not the Iodide near the Methyl group.  Also, a concern with the starting material as it seemed to be quite expensive.  I may not have checked a reliable source, but according to ONE site I checked, it was about 5g's for 95USD, which is a bit outside my wallet.

Please let me know if this looks promising as at all or if there are reactions similar to this that I may read/go over.
« Last Edit: July 09, 2012, 02:18:11 AM by thecriscoking »

akcom

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Re: Route to Amphetamine
« Reply #1 on: July 09, 2012, 02:30:43 AM »
This is way too complicated.  If you really want to make amphetamines, the way to go is through phenyl-2-propanone or phenyl-2-nitropropene

Enkidu

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Re: Route to Amphetamine
« Reply #2 on: July 09, 2012, 01:14:36 PM »
Most of those intermediates are either unstable or simply don't exist. One of the rules is to include 'prior art,' i.e., patents, journals, or experiments, along with your scheme. Nearly everything before the FC step is bunk.

FC with protected amino acids is possible. You could save yourself a lot of trouble by starting with alanine.

POSEIDON

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Re: Route to Amphetamine
« Reply #3 on: July 09, 2012, 04:32:42 PM »
read this book ,  Organic_Synthesis__The_Disconnection_Approach__Second_Edition., is here in the e-book library .

look this pdf , is the old way
The chemists are a strange class of mortals, impelled by an almost insane impulse to seek their pleasures amid smoke and vapour, soot and flame, poisons and poverty; yet among all these evils I seem to live so sweetly that may I die if I were to change places with the Persian king.
— Johann Joachim

carl_nnabis

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Re: Route to Amphetamine
« Reply #4 on: July 09, 2012, 06:26:52 PM »
i would expect to see the intermediate you want to react with benzene in a polimerized structure, i mean, amine, halide AND ketone, thats at least  2 ways to polimerize
"It's like the drug trip I saw when I was on that drug trip!"

thecriscoking

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Re: Route to Amphetamine
« Reply #5 on: July 09, 2012, 10:53:46 PM »
Thank you everyone for the response.

Quote from: akcom on July 09, 2012, 02:30:43 AM
This is way too complicated.  If you really want to make amphetamines, the way to go is through phenyl-2-propanone or phenyl-2-nitropropene

This is probably true.  I was only trying to propose an alternate route and check the validity of it.  Maybe it could excite thought in others, but according to the other responses this may be too basic.  :P

Quote from: Enkidu on July 09, 2012, 01:14:36 PM
Most of those intermediates are either unstable or simply don't exist. One of the rules is to include 'prior art,' i.e., patents, journals, or experiments, along with your scheme. Nearly everything before the FC step is bunk.

FC with protected amino acids is possible. You could save yourself a lot of trouble by starting with alanine.

Could you elaborate as to why they do not exist/are unstable?  I can see the unstability in one but just for learning purposes what would you be looking for?  I was totally unaware that this compound (alanine) existed. Haha.  I was trying to "reverse engineer" a synthesis so that maybe it could be prepare for relatively cheap and with readily available chemicals, I definitely over looked some aspects. 

Quote from: POSEIDON on July 09, 2012, 04:32:42 PM
read this book ,  Organic_Synthesis__The_Disconnection_Approach__Second_Edition., is here in the e-book library .

look this pdf , is the old way


Thank you for the idea, I will check this book out now.  Also, I have read this method on the erowid archives but had trouble with a route to HgCl2.  I have not done much research on the topic  though so this method seems doable.  I understand mercury and it's salts are fairly toxic and I am pretty sure mercury is cheap.


Quote from: carl_nnabis on July 09, 2012, 06:26:52 PM
i would expect to see the intermediate you want to react with benzene in a polimerized structure, i mean, amine, halide AND ketone, thats at least  2 ways to polimerize

I see where you are coming from.  I am not very sure about polymerization so this one is out of my league.

Also let it be known that I am not simply trying to synthesis amphetamine as much as learn the chemistry.  If the chance occurs where I attempt any synthesis it would be on such a small scale to simply attempt and learn. 

Enkidu

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Re: Route to Amphetamine
« Reply #6 on: July 10, 2012, 12:28:21 PM »
I'm moving this topic to The Den.

Quote from: thecriscoking on July 09, 2012, 10:53:46 PM
Could you elaborate as to why they do not exist/are unstable?

As carl noted, many of the compounds are prone to polymerization or intramolecular cyclization to epoxides or aziridines. The polymerization is very simple theoretically: since you aren't working with one, single molecule, your haloalkanes will link up with their aminated brothers.

A pedantic note: the starting molecule is 1-chloropropene, not pentene.

Also, many of those compounds are hazardous. Many halo compounds are lachrymators at best and acutely toxic at worst. Working with anhydrous ammonia is no picnic. Additionally, Cr(VI) is toxic and a hazard to the environment. But, I guess 'hazardous' is a bit relative. You'll have a hard time finding 100% green routes.

Edit: I forgot to mention that the geminal halo alcohol probably doesn't exist.
« Last Edit: July 11, 2012, 02:57:49 PM by Enkidu »

atara

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Re: Route to Amphetamine
« Reply #7 on: July 11, 2012, 06:03:59 PM »
I don't see how a novice could have invented this. This thread looks like the work of someone reasonably skilled who is intentionally trolling.

Though, it reminds me of an old idea I had: FC alkylation with lactaldehyde should give a vicinal diol that eliminates to an arylacetone. More reliable than Mn (III) acetate and way safer than bromoacetone.
« Last Edit: July 11, 2012, 06:26:41 PM by atara »

thecriscoking

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Re: Route to Amphetamine
« Reply #8 on: July 11, 2012, 07:31:51 PM »
Quote from: Enkidu on July 10, 2012, 12:28:21 PM
As carl noted, many of the compounds are prone to polymerization or intramolecular cyclization to epoxides or aziridines. The polymerization is very simple theoretically: since you aren't working with one, single molecule, your haloalkanes will link up with their aminated brothers.

A pedantic note: the starting molecule is 1-chloropropene, not pentene.

Also, many of those compounds are hazardous. Many halo compounds are lachrymators at best and acutely toxic at worst. Working with anhydrous ammonia is no picnic. Additionally, Cr(VI) is toxic and a hazard to the environment. But, I guess 'hazardous' is a bit relative. You'll have a hard time finding 100% green routes.

Edit: I forgot to mention that the geminal halo alcohol probably doesn't exist.

Thank you for clearing that up, I understand.  My bad with the naming, I can't believe I misnamed sometimes so simple.  If I have to deal with some hazardous chemicals, I am okay with this, but of course I would like to do this as little as possible.


Quote from: atara on July 11, 2012, 06:03:59 PM
I don't see how a novice could have invented this. This thread looks like the work of someone reasonably skilled who is intentionally trolling.

Though, it reminds me of an old idea I had: FC alkylation with lactaldehyde should give a vicinal diol that eliminates to an arylacetone. More reliable than Mn (III) acetate and way safer than bromoacetone.
Haha, I'm not sure if that's a compliment or not   ;D
I can assure you I am no troll.  I simply was trying to create an alternate route, perhaps with as little purchasing as possible as poor students like myself are not coming across any walking around money  :P  But you can tell I still have very much to learn, but I can't stay I did attempt ha

Quantum Dude

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Re: Route to Amphetamine
« Reply #9 on: September 09, 2012, 11:30:21 PM »
Quote from: carl_nnabis on July 09, 2012, 06:26:52 PM
amine, halide AND ketone

Its actually an acyl halide.

carl_nnabis

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Re: Route to Amphetamine
« Reply #10 on: September 09, 2012, 11:42:24 PM »
acyl? I thought an alkyl?
edit: no i assumed acyl stands for an aromatic group, but it means just RCO where R could also be aliphatic  :-[ ::) havent seen that it is an acid chloride
« Last Edit: September 09, 2012, 11:49:42 PM by carl_nnabis »
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Assyl Fartrate

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Re: Route to Amphetamine
« Reply #11 on: September 10, 2012, 02:02:19 AM »
Beta-haloketone... not acyl halide... you missed a carbon.
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carl_nnabis

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Re: Route to Amphetamine
« Reply #12 on: September 10, 2012, 02:14:09 AM »
How about 2-aminopropionylchloride?  8)
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Quantum Dude

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Re: Route to Amphetamine
« Reply #13 on: September 10, 2012, 02:28:45 AM »
Quote from: Assyl Fartrate on September 10, 2012, 02:02:19 AM
Beta-haloketone... not acyl halide... you missed a carbon.

Its an acyl halide, youre seeing too many carbons. A beta-halo ketone would show the halide functional group on a carbon in beta position with respect to the carbonyl FYI.

Assyl Fartrate

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Re: Route to Amphetamine
« Reply #14 on: September 10, 2012, 03:37:30 AM »
Assyl won't even bother trying to explain the state of mind required for him to believe NH2 to be a halogen.

You're right.
Someone Who Is Me
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