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Synthesis 1995; 1995(2): 150-152
DOI: 10.1055/s-1995-3875
short paper
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Synthesis of Primary Amines Using Potassium 1,1,3,3-Tetramethyldisilazide as Aminating Agent of Alkyl Halides

Shinichi Itsuno* , Takahiro Koizumi, Chisa Okumura, Koichi Ito
  • *Department of Materials Science, Toyohashi University of Technology, Toyohashi 441, Japan
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Publication Date:
31 December 2000 (online)

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A one-pot synthesis of various primary amines is described. Potassium 1,1,3,3-tetramethyldisilazide, prepared from 1,1,3,3-tetramethyldisilazane and potassium hydride, reacts with alkyl bromides, iodides, tosylates, benzylic chlorides, and allylic chlorides to give the corresponding N,N-bis(dimethylsilyl)amines in high yields. Subsequent deprotection of the dimethylsilyl group was performed under mildly acidic conditions to afford primary amines. This method was also applied to the preparation of aminomethylated cross-linked polystyrene.

primary amines - tetramethyldisilazide - alkyl halides - amination - aminomethylated polystyrene