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Expedient five-step synthesis of SIB-1508Y from natural nicotine

Florence F Wagner1, Daniel L Comins

  • 1Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.

The Journal of Organic Chemistry
|October 27, 2006
PubMed

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...