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N-alkylation of amides with alkyl halides?
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+ Biochemistry
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Matshidiso Sekwala
N-alkylation of amides with alkyl halides?
The amide nitrogen is not a good nucleophile to react. But it can become nucleophilic in the form of $\mathrm N^-$ as a conjugate base of a weaker acid. This means that you need a strong enough base to deprotonate the amide. Some standard conditions are NaH in THF or DMF, or n-BuLi, LDA and the like in THF/ether etc.
The amide nitrogen is not a good nucleophile to react. But it can become nucleophilic in the form of $\mathrm N^-$ as a conjugate base of a weaker acid. This means that you need a strong enough base to deprotonate the amide. Some standard conditions are NaH in THF or DMF, or n-BuLi, LDA and the like in THF/ether etc.
The amide nitrogen is not a good nucleophile to react. But it can become nucleophilic in the form of $\mathrm N^-$ as a conjugate base of a weaker acid. This means that you need a strong enough base to deprotonate the amide. Some standard conditions are NaH in THF or DMF, or n-BuLi, LDA and the like in THF/ether etc.
The amide nitrogen is not a good nucleophile to react. But it can become nucleophilic in the form of $\mathrm N^-$ as a conjugate base of a weaker acid. This means that you need a strong enough base to deprotonate the amide. Some standard conditions are NaH in THF or DMF, or n-BuLi, LDA and the like in THF/ether etc.
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Sure, there are a number of ways to do this with copper, iridium, or palladium catalysts. This link should hopefully be helpful.
http://www.organic-chemistry.org/synthesis/C1N/amides2.shtm
Sure, there are a number of ways to do this with copper, iridium, or palladium catalysts. This link should hopefully be helpful.
http://www.organic-chemistry.org/synthesis/C1N/amides2.shtm
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