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Author Topic: Tosylate Salt Of 1-(1-Cyclohexenyl) Butylamine ?  (Read 2307 times)

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Bwiti

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Tosylate Salt Of 1-(1-Cyclohexenyl) Butylamine ?
« on: June 05, 2002, 02:16:00 PM »
Goddamn fuckin' fuck. Alright, lets say 196g cyclohexanone and 146g n-butylamine was added to 600ml benzene, then it was distilled until all water had been removed. I want to convert this into a tosylate salt. This is done by adding p-toluenesulfonic acid monohydrate to toluene and distilling until all water is removed, and this is added to the 1-(1-cyclohexenyl) butylamine. What I'm dying to know is how much p-toluenesulfonic acid monohydrate do I add to the toluene? Any help would be much appreciated! 8)
Love my country, fear my government.
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Osmium

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I think you should learn about moles and ...
« Reply #1 on: June 05, 2002, 02:53:00 PM »
I think you should learn about moles and molecular weights and stuff.
I'm not fat just horizontally disproportionate.
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Bwiti

  • Guest
Dammit!
« Reply #2 on: June 05, 2002, 10:59:00 PM »
Dammit! I was hoping that no one would bring up my obvious weakness.. Alright, so is it as easy as reacting 1 mole of 1-(1-cyclohexenyl) butylamine with 1 mole p-toluenesulfonic acid? Then I react 1 mole phenyl-magnesium-iodide with 1 mole of the tosylate? I wish that my chemistry teacher in highschool wasn't such an uptight shit-fuck, then I wouldn't have to feel so retarded. :P
Love my country, fear my government.
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Rhodium

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But do you really want the imine tosylate (is ...
« Reply #3 on: June 05, 2002, 11:04:00 PM »
But do you really want the imine tosylate (is that really stable)? You aren't trying to do a tosic acid catalyzed condensation of butylamine and cyclohexanone with azeotropic removal of the water in the dean-stark?

But if you want to make a salt, yes - use one mole of each.
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Bwiti

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Frustrated
« Reply #4 on: June 06, 2002, 12:52:00 AM »
"But do you really want the imine tosylate"

  No, I'd rather smash my fingers with a hammer. My problem is that all patents that use a plain-old 1-(1-cyclohexenyl)amine (CHA) react it with phenyl-lithium. I want to use Mg, but I can't find one example that uses phenyl-magnesium on a CHA. In the patents, phenyl-Mg's always reacted with nitriles and in US3192219(example 1) it's reacted with the tosylate salt. Will phenyl-Mg work? If so, then why can't I find ANY examples?
Love my country, fear my government.
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Bwiti

  • Guest
Any flat-out guesses? :-P
« Reply #5 on: June 07, 2002, 06:08:00 AM »
Any flat-out guesses? :P
Love my country, fear my government.
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Osmium

  • Guest
I don't understand what you're asking.
« Reply #6 on: June 07, 2002, 11:27:00 AM »
I don't understand what you're asking.
Have you seen this one already?

https://www.thevespiary.org/rhodium/Rhodium/chemistry/pcp/enam_synth.html


I'm not fat just horizontally disproportionate.
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Bwiti

  • Guest
Oops! I was getting confused between ...
« Reply #7 on: June 08, 2002, 03:29:00 AM »
Oops! I was getting confused between imines/enamines.. Thanks, question answered. :P
Love my country, fear my government.
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Bwiti

  • Guest
Btw
« Reply #8 on: June 08, 2002, 04:25:00 PM »
Btw, would a little excess of anhydrous p-toluenesulfonic acid hinder the effectiveness of the phenyl-Mg-bromide?  
Love my country, fear my government.
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Osmium

  • Guest
Yes!
« Reply #9 on: June 08, 2002, 07:50:00 PM »
Yes!
I'm not fat just horizontally disproportionate.
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