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Author Topic: Phenmetrazine  (Read 236 times)

Happyman

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Phenmetrazine
« on: August 14, 2009, 04:01:27 AM »
I need help translating a German patent. And yeah I ripped it from Wetdreams.

ORIGINAL

N-Oxyäthylmorpholin (I) [this is a misprint, it should say N-Oxyäthylnorephedrin instead.]

20 g. DL-Norephedrin als freie Base werden in etwa 50 ml. Äthylenchlorhydrin 8-10 Stunden auf dem Wasserbade bei 85-95° erhitzt. Nach Erkalten wird mit Äther verdünnt, wobei das Hydrochlorid des N-Oxyäthylmorpholin [N-Oxyäthylnorephedrin] in 96-98% Ausbeuten auskristallisiert. Es wird abgesaugt und mit Äther gewaschen. Schmp.: 166-168°, freie Base, Schmp.: 110-112°.

Durch Lösen in Isopropanol und Zusatz von Äther kann I umkristallisiert werden. Für die Weiterverarbeitung ist eine Umkristallisation jedoch nicht nötig. Das Präparat ist schneeweiß.

2-Phenyl-3-methyl-morpholin (II)

20 g. des Hydrochlorids von I werden in 100 ml. Tetralin suspendiert, 0,5 bis 1 g. p-Toluolsulfonsäure werden zugefügt. Unter Rühren und Durchleiten eines Stickstoffstromes wird auf 200-210° erhitzt, wobei das abgespaltene Wasser abdestilliert und durch einen Wasserabscheider aufgefangen wird; so bald die berechnete Menge Wasser aufgefangen ist, wird die Erhitzung abgestellt. Dauer 5-7 Stunden. Nach Erkalten kristallisiert das Hydrochlorid von II aus. Schmp.: 180-182°, wird durch Lösen in wenig Alkohol und Zusatz von Aceton und Äther gereinigt.

J. prakt. 293, 12 (1963)

Google translate gives me

20 g. dl-norephedrine as a free base in 50 ml Äthylenchlorhydrin about 8-10 hours on the water bath at 85-95 ° heat. After cooling, is diluted with ether, and the hydrochloride of N-Oxyäthylmorpholin [N-Oxyäthylnorephedrin] in 96-98% yields crystallized. There will be removed and washed with ether. Schmp.: 166-168 °, free base, Schmp.: 110-112 °.

By dissolution in isopropanol and addition of ether umkristallisiert I can be. For further Umkristallisation is not necessary. The drug is snowy white.

2-Phenyl-3-methyl-morpholine (II)

20 g. of the hydrochloride of I in 100 ml Tetralin suspended from 0.5 to 1 g. p-Toluolsulfonsäure are added. Under stirring introduction, and a nitrogen flow is heated to 200-210 °, with the water off abdestilliert and a water is absorbed, as soon as the calculated amount of water absorbed, the heating off. Duration 5-7 hours. After cooling, the crystallized hydrochloride of II. Schmp.: 180-182 °, is determined by dissolving in a little alcohol and the addition of acetone and ether cleaned.

My Questions being is Äthylenchlorhydrin ethylene chlorohydrin?
I am 99% sure that p-Toluolsulfonsäure is p-Toluenesulfonic acid but got to be sure, and what is N-Oxyäthylnorephedrin?

IceCold

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Re: Phenmetrazine
« Reply #1 on: August 14, 2009, 01:48:43 PM »
I can confirm that p-Toluolsulfonsäure is p-toluolsulfonic acid. Don't know for sure about the other one.

basstabone

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Re: Phenmetrazine
« Reply #2 on: August 14, 2009, 02:05:13 PM »
Äthylenchlorhydrin is in fact ethylene chlorohydrin. This seems like a very interesting molecule! Was reading up on it a bit and would love to see it made

jon

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Re: Phenmetrazine
« Reply #3 on: September 06, 2009, 08:06:35 AM »
that would be n-hydroxyethylnorephedrine.
that second step seems tedious and harsh conditions are used.
it could be replaced by performing the cyclization in cold h2so4.
i'm a little confused, water is absorbed into what? a drying tube is affixed?
they don't say.
hmmm it looks like ethylene chlorohydrin is a synthon for ethylene oxide and this adds to the nitrogen in  a nucleophilic manner.
ethylene chlorhydridrin is made from ethylene glycol using hydrochloric acid at high temperatures.
yeilds are low !0%
search sm for more.
« Last Edit: September 06, 2009, 09:05:13 AM by jon »

ausser_betrieb

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Re: Phenmetrazine
« Reply #4 on: September 11, 2009, 05:07:07 PM »
I translated it, hope everything is clear now.

(I) N-Oxyäthylnorephedrin

20 g. norephedrine as free base are heated in about 50ml ethylene chlorohydrin to 85-95°C for about 8 to 10h.
After Cooldown its diluted with ether, the N-Oxyäthylnorephedrin HCl crystallizes in a 96-98% yield.
Its filtered and washed with ether. MP: 166-168°C free base MP: 110-112°C

Solvating in IPA and adding ether could be used to recrystallize, but isnt nescessary for the next step.
Product is snow-white.

(II) 3-methyl-2-phenylmorpholine
20g of the HCl from I are suspended in 100ml tetralin, 0,5 to 1g p-toluolsulfonic acid are added.
Under stirring and a stream of Nitrogen its heated to 200 - 210°C, the developing Water is distilled off and catched, as soon as the calculated amount of water is catched the heat is switched off. Duration 5-7 hours.
After cooldown the HCl from II crystallizes out. MP: 180-182°C
It is solvated in a small amount of alcohol and cleared by adding acetone and ether.

J. prakt. 293, 12 (1963)

Sedit

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Re: Phenmetrazine
« Reply #5 on: September 11, 2009, 05:41:17 PM »
As far as the 2-Chloroethanol is concerned I would think much better then 10% yeilds could be had if one was able to subject Ethylene to a concentrated NaOCl solution.  

BTW:Happyman when subjecting any text to google translate convert the Ä and ü type letters to there corrisponding letter. These are just symbols to the google translator and translate as a misspelled word.


Edit

Here is the same text translated with the letters fixed, It pretty much answered every question posed in this threed.


20 g. DL-norephedrine as the free base is heated in 50 ml ethylene chlorohydrin 8-10 hours on the water at 85-95 °. After cooling, diluted with ether, crystallized with the hydrochloride of N-Oxyathylmorpholin [N-Oxyathylnorephedrin] in 96-98% yields. It is filtered and washed with ether. Mp: 166-168 °, a free base, mp: 110-112 °.

By dissolving in isopropanol and addition of ether I can be recrystallized. For the reprocessing are recrystallization is not Obtaining required. The product is white.

2-phenyl-3-methyl-morpholine (II)

20 of the hydrochloride of I g. are suspended in 100 ml of tetralin, 0.5 to 1 g p-toluenesulfonic acid are added. With stirring and passing a nitrogen stream is heated to 200-210 °, with the split-off water is distilled off and collected by a water separator, as soon as the calculated amount of water is absorbed, the heating is turned off. Duration 5-7 hours. After cooling, the hydrochloride crystallizes out of IIS. Mp: 180-182 °, is purified by dissolving in a little alcohol and the addition of acetone and ether.
« Last Edit: September 11, 2009, 05:48:33 PM by Sedit »
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