[Messi]

Hi,

I have a secondary amine complexed with hydrochloric acid. How could I liberate the hydrochloric acid so I would just be left with my secondary amine?

This would be of great *delete me*

[discodermolide]

Treat it with sodium hydroxide solution, then extract it into a suitable solvent. Remove the solvent and you have it.

[Messi]

Treat it with sodium hydroxide solution, then extract it into a suitable solvent. Remove the solvent and you have it.

Here is a proposed procedure, let me know what you think:

1) Weigh out required amount of secondary amine complexed with HCl.

2) Add a one molar equivalence amount of Sodium Hydroxide to my secondary amine complexed with HCl.

3) Add dichloromethane to the solution and shake.

4) The two solvents will be water and dichloromethane. Remove the dichloromethane extracts via an extraction. Dichloromethane is more dense, so it will be in bottom of seporatory funnel.

5) Once dichloromethane solvent is extracted, remove the solvent via a rotavap machine.

Take NMR to confirm!

[discodermolide]

Looks ok, you can easily use a slight excess of NaOH if your molecule will tolerate it. It does not have to be equivalent amounts, use 1.1-1.2 equ. NaOH.

[Messi]

Excellent. Thanks!

Would using dichloromethane or diethylether be better for better extraction?

I do know dichloromethane is more dense than water... which might be nice..