The Hive => Chemistry Discourse => Topic started by: Bwiti on June 05, 2002, 02:16:00 PM
Title: Tosylate Salt Of 1-(1-Cyclohexenyl) Butylamine ?
Post by: Bwiti 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.
Title: I think you should learn about moles and ...
Post by: Osmium 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.
Title: Dammit!
Post by: Bwiti 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.
Title: But do you really want the imine tosylate (is ...
Post by: Rhodium 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.
Title: Frustrated
Post by: Bwiti 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.
Title: Any flat-out guesses? :-P
Post by: Bwiti on June 07, 2002, 06:08:00 AM
Any flat-out guesses? :P Love my country, fear my government.
Title: I don't understand what you're asking.
Post by: Osmium on June 07, 2002, 11:27:00 AM
I don't understand what you're asking. Have you seen this one already?