[mary248]

Hi
I have an HCl amine salt and I am trying to methylate the amine, however since it is present as the HCl salt I am having difficulty performing the reaction so I was wondering what is the best method to convert the salt to the free amine so I can carry out my reaction??

Thanks a lot in advance for your help...

[Babcock_Hall]

The answer might depend upon the compound you are methylating.

[wildfyr]

What do you think is the best way to deprotonate the amine? We ask that people show us their attempt before we answer. In my mind there is a pretty straightforward technique that everyone does in Ochem 1 lab.

[mary248]

I have tried using TEA as an initial step but reaction mixture becomes one hot mess when analysed by LCMS hence why i want to convert it to free amine before i do my reaction

[mary248]

The answer might depend upon the compound you are methylating.

Is an aniline derivative with a pentyl amine chain.....i only want to methylate the aliphatic chain....i have tried using TEA but reaction mixture becomes inseparable and complicated  and also tried deprotonating with potassium carbonate but no luck...I am methylating with paraformaldehyde, sodium borohydride and TFA

[OrganicDan96]

what about sodium hydroxide?

[Enthalpy]

For my personal information please:
As the reaction with the added base produces water, and the wanted amine (for instance azetidine) may be soluble in or miscible with water, how can the best amount of amine be recovered?
Supply CaO or Na₂O instead of NaOH?
Separate the freed amine somehow?
Thanks!