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OMONJIATE ELIAB PATRICK

N di- Methylation of a secondary Amide

Donna Baker  Follow
how about deptotonate amide with strong base then treat with MeI, then hydrolyse and methylate again

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Chris Hirst  Follow
Don't you need a base like nBuLi or LDA to deprotonate an amide?

I've always been under the impression that reductive amination is the "easy" way to get secondary amines. You can do it twice from ammonia with acetaldehyde to get diethylamine for instance. Doesn't get much greener than that (aside from the NaBH4). I think that's what kriggy was getting at.

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Christopher Proescher  Follow
Hydrolyze first and then use formic acid/formaldehyde to get dimethylation. Probably even methylation with MeI could work fine if you carefully control the conditions

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