What type of reaction converts a secondary amine to primary amine?

[Kushal]

Homework Statement

Part of a long question:

suggest the type of reaction occurring:

(C₆H₅)₃C-NH-CH(CH₃)-CO-NHCH₂COOH -----> (C₆H₅)₃C-H + NH₂-CH(CH₃)-CO-NHCH₂COOH

The Attempt at a Solution

what i got in mind is that it could a free radical substitution reaction?! using H₂...

and i also realized that the reaction is converting a secondary amine to a primary amine... i don't know how it can be done... although converting a primary amine to a secondary one can easily be done by reacting the amine with an alkyl halide... nucleophilic substitution reaction.


thnks

 

[chemisttree]

What element has been added to your compound in this reaction? Balance the equation and it will speak for itself.

 

[Kushal]

it seems that hydrogen has been added. but i can't find any type of reaction involving hydrogen like this.

i would rather think of a species which is a stronger nucleophile than the 'ammonium stuff' since the carbon attached to the - NH - has a partial positive charge.

but could it be a reducing reaction?!

 

[chemisttree]

it seems that hydrogen has been added. but i can't find any type of reaction involving hydrogen like this.

i would rather think of a species which is a stronger nucleophile than the 'ammonium stuff' since the carbon attached to the - NH - has a partial positive charge.

but could it be a reducing reaction?!

Yes.

You could also call it a deamination reaction (if you were interested in the alkyl/aryl group) or a dealkylation reaction (if you were interested in the amine fraction of the molecule).

I would call it an N-trityl deprotection reaction of the dipeptide N-(trityl)alanine-glycine.
Deprotection of trityl-substituted peptides can be accomplished by treatment with alcoholic acid. Not a free radical process.

 

[Kushal]

ooo ok... the question is from a past past past exam paper...lol... i guess we won't be getting such questions in the finals... because i didn't find any deamination or dealkylation reaction in the syllabus...

thnks again...:)