joe_aldehyde
Hazard to Self
Posts: 68
Registered: 26-3-2005
Member Is Offline
Mood: what is mood?
|
|
Secondary Amines from Alkylhalides via N-Alkyl-sulfonamides?
this looks promising:
reacting a secondary alkylhalide with a n-alkyl-sulfonamide and final cleavage with HBr/Phenol should lead to the secondary amine. what i have found
so far is:
http://www.orgsyn.org/orgsyn/default.asp?formgroup=basenpe_f...
these are not free, but maybe someone can "look them up" 
http://www3.interscience.wiley.com/cgi-bin/summary/109869493...
http://www.rsc.org/CFmuscat/intermediate_abstract.cfm?FURL=/...
http://yakushi.pharm.or.jp/abst_2005/No1/no1.html
any ideas on the cleavage of the sulfonamide? it seems that this can only be effected under harsh conditions.
|
|
|
ChemPhile
Harmless
Posts: 9
Registered: 1-11-2004
Member Is Offline
Mood: No Mood
|
|
How about the Raney Ni/H2 for the catalytic cleavage of the sulphonamide
|
|
|
enima
Hazard to Self
Posts: 98
Registered: 1-12-2004
Member Is Offline
Mood: No Mood
|
|
alternative method maybe?
How about oxidizing the secondary halide to the ketone via V2O5/H2O2. Reaction of the ketone with hydroxylamine to make the oxime and the reduction of
the oxime with activated zinc and ammonium formate/chloride.
|
|
|
joe_aldehyde
Hazard to Self
Posts: 68
Registered: 26-3-2005
Member Is Offline
Mood: what is mood?
|
|
enima, do you have details on that oxidation?
i also have methylamine (instead of hydroxylamine because i want the n-methylated amine), but i wonder what is the best method to reduce the imine
formed by reductive amination. i'm not very comfortable with Hg salts.
|
|
|
enima
Hazard to Self
Posts: 98
Registered: 1-12-2004
Member Is Offline
Mood: No Mood
|
|
Oxidation method
NaBH4 works really well at reducing the imine to the amine, I can post the proceedure for that as well if you want.
Below I attached the oxidation method. (PDF form)
Attachment: BenzylAlcohol oxidation with V2O5 Catalyst.pdf (189kB)
This file has been downloaded 11199 times
|
|
|
joe_aldehyde
Hazard to Self
Posts: 68
Registered: 26-3-2005
Member Is Offline
Mood: what is mood?
|
|
yes, please post the procedure. i'm especially interested in processes that don't require the absence of aqueous solutions (eg. menh2 40%
aq.)
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
