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Author: Subject: Pyrrolidine/Putrescine?
morsagh
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[*] posted on 4-6-2016 at 05:37
Pyrrolidine/Putrescine?

What is more favorable reaction in reaction of 1,4-dibromobutane and excess of ammonia. There will be more of 1,4-diaminobutane or pyrrolidine? Any catalyst to decrease formation of pyrrolidine?
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NitreRat
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[*] posted on 4-6-2016 at 10:21


If your desired product is 1,4-diaminobutane you could use potassium phthalimide in the Gabriel synthesis reaction.

EDIT: Or alternatively, you could use hexamine in the Delépine reaction.

[Edited on 6/4/2016 by NitreRat]
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morsagh
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[*] posted on 4-6-2016 at 11:34


Can be used maleimide instead for protecting?
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morsagh
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[*] posted on 4-6-2016 at 11:41


So in synthesis of secondary amines can be used N substituted acetamide?
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NitreRat
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[*] posted on 4-6-2016 at 14:51


Quote: Originally posted by morsagh  
So in synthesis of secondary amines can be used N substituted acetamide?


Yes, you can dialkylate an amide to form a tertiary amide which can then be hydrolyzed to yield a secondary amine.

The benefit of using potassium pthalimide is that it reacts very easily with alkyl halides. The reaction of an alkyl halide with an amine/amide generates the corresponding hydrohalic acid which can react with the amine/amide so a base such as Triethylamine or K2CO3 has to be used to remove the acid as it's formed. With potassium pthalimide the potassium salt is formed instead of the acid, driving the reaction to completion and avoiding potential side-reactions.

[Edited on 6/4/2016 by NitreRat]
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morsagh
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[*] posted on 5-6-2016 at 02:31


Are there any reference for alkylation of N-alkylamides to N,N-dialkylamides? Does it need some stronger base or K2CO3 is enough. What solvent should be used.
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CuReUS
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[*] posted on 5-6-2016 at 06:05


according to this german paper,both pyrrolidine and putrescine will be formed when NH3 is reacted with 1,4-dibromobutane
http://onlinelibrary.wiley.com/doi/10.1002/cber.19370700522/...

Gabriel reaction is the way to go - http://www.google.com/patents/US2757198
Morsagh, are you looking for novel routes to putrescine ? because the easiest way IMO is the decarboxylation of ornithine
reference - http://onlinelibrary.wiley.com/doi/10.1002/cber.189803103108...
video-https://www.youtube.com/watch?v=UAldEzWpr_A
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Nicodem
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6-6-2016 at 12:36

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