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Synthesis 1990; 1990(2): 122-124
DOI: 10.1055/s-1990-26805
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A Convenient Synthesis of Primary Amines Using Sodium Diformylamide as A Modified Gabriel Reagent

Han Yinglin* , Hu Hongwen
  • *Chemistry Department, Najing University, Nanjing 210008, People's Republic of China
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Publikationsdatum:
17. September 2002 (online)

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Sodium diformylamide (1) was used as a convenient substitute for phthalimide in the Gabriel synthesis of primary amines. Reagent 1 undergoes smooth N-alkylation with alkyl halides or p-toluenesulfonates 2 in acetonitrile or dimethylformamide to give the corresponding N,N-diformylalkylamines 3 in good yields, except with alkylating agents which are susceptible to base-catalyzed elimination. The formyl group of 3 can be easily removed by hydrochloric acid to give the corresponding alkylamine hydrochlorides 5 or free alkylamines 4.