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Mukund P Sibi1, Hikaru Hasegawa

  • 1Department of Chemistry and Center for Protease Research, North Dakota State University, Fargo, ND 58105, USA.

Organic Letters
|September 27, 2002
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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...