joe_aldehyde - 5-4-2005 at 15:08
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 - 8-4-2005 at 18:43
How about the Raney Ni/H2 for the catalytic cleavage of the sulphonamide
alternative method maybe?
enima - 9-4-2005 at 10:20
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 - 9-4-2005 at 12:58
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.
Oxidation method
enima - 9-4-2005 at 18:09
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 11210 times
joe_aldehyde - 10-4-2005 at 05:28
yes, please post the procedure. i'm especially interested in processes that don't require the absence of aqueous solutions (eg. menh2 40%
aq.)