Do beta-keto amphetamines racemise easily if stored in a protic solvents?

[aced126]

What are everyone's thoughts on whether the title is true? Examples of compounds which fall into that category are bupropion, MDMC, 4-MMC and many others. I would presume the S isomers of each of these would be much more centrally active.

 

[Solipsis]

Don't you think that enol equilibrium would say yes to this question?

(Even if its SN2 seems irrelevant, but that may be nonsense pertaining to the matter)

 

[aced126]

That's what I thought, I just wanted confirmation. So this means storage of these types of compounds in protic solvents is out of the question?

 

[adder]

Yes, they will racemise in protic solvents.