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Bromoderivative of diethylene triamine-any idea or suggestion?

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barcrphd:
i am trying to synthesize the following ligand for quite a long time. but i could not get it as of yet. i am thinking of giving it a fresh try. but not before getting some suggestions from you people..

please suggest your ideas....

saltyf:
I think this can be extremely difficult, for the CH2-Br moiety can easily reaction with the primary amine via an intramolecular SN2 mechanism.

barcrphd:
ofcourse, it is difficult, but not due to the problem that you have suggested. infact, this is the target ligand. but i dont want it in this form. ok, to avoid confusion, i will give a new structure. see the following structure. even this will do. i will then remove the phthalimide protection to generate the amine.

HP:
I suggest you following synthesis:
Ethylene triamine + phatalymide -->protection of both primary NH2 groups as your own suggestion..
Next Michael addition of CH2=CHCOOH(acrylic acid) to free secondary amine obtaining the coresponding beta-amino carboxylic acid derivate.
Then you may try Borodin reaction (known also as Hunsdiecker or Hunsdiecker-Borodin reaction)  of Ag-salt this carboxylic acid with Br2/CCl4 to desired product beta-ethylbromo aduct + AgBr.
Whish you success !

wereworm73:
I'd stay with the phthalimide version since you don't have strongly nucleophilic groups on the same molecule as the brominated carbon. 

The problem with the bromoderivative of diethylene triamine is that the NH2 groups can do a nucleophilic attack on the brominated carbon.  Because of this, these molecules can react with themselves to form piperazine derivatives (or polymers, if the NH2 group and the brominated carbon are on different molecules).

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