RE: ORGLIST: N-alkylation

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From: will jones (willjones46$##$hotmail.com)
Date: Mon Oct 24 2005 - 04:49:36 EDT


Carry out reaction with TEA instead of KCarb, or

what about using 2-bromoacetaldehyde with Na(OAc)3BH with 0.5eq. acetic
acid? I use Na(OAc)3BH for all of my N-alkylations.

Have you tried refluxing the reaction?

Will




>From: "madhav balakrishna mallia" <madhavmallia$##$rediffmail.com>
>Reply-To: madhav balakrishna mallia <madhavmallia$##$rediffmail.com>
>To: everybody$##$orglist.net
>Subject: ORGLIST: N-alkylation
>Date: 22 Oct 2005 17:47:46 -0000
>
>hello
>i need some suggestions regarding N-alkylation. the substrate is diethylene
>triamine where both the primary amine groups are protected with
>phthalimide. i want to N-alkylate the remaining secandary amine with 1,2
>dibromoethane i did the reaction using anhy potassium carbonate in
>acetonitrile. but the reaction is not proceeding. do anyone has an idea,
>why it is not going and is there a reagent which can drive this reaction
>without affecting the protective phthalimide group?
>thanking u in advance
>
>
>
>Madhava B Mallia
>Scientific Officer D
>BHABHA ATOMIC RESEARCH CENTRE
>Mumbai


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