Synthesis of Amines

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Author:
enger91
ID:
85455
Filename:
Synthesis of Amines
Updated:
2011-05-12 13:02:10
Tags:
amine organic chemistry
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Description:
University of MN Twin Cities, CHEM 2302
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  1. Phthalimide synthesis
    phthalimide + 1)KOH 2)primary alkyl halide 3)H2N-NH2, heat-> primary amine
  2. phthalimide --> primary amine
    • 1)KOH
    • 2)primary alkyl halide
    • 3)H2N-NH2, heat
  3. phthalimide + 1)KOH 2)primary alkyl halide 3)H2N-NH2, heat->
    primary amine
  4. R-OH + 1)TsCl, pyridine 2)NaN3 (aq)->
    R-N3 (azide)
  5. R-N3 + 1)LiAlH4 2)H2O->
    R-NH2 (primary amine)
  6. R-OH --> R-N3
    • 1)TsCl, pyridine
    • 2)NaN3 (aq)
  7. R-N3 --> R-NH2
    • 1)LiAlH4
    • 2)H2O
  8. alkyl halide + NaN3->
    R-N3
  9. alkyl halide --> R-N3
    NaN3
  10. R-OH + 1)TsCl, pyridine 2)NaCN->
    R-CN
  11. R-OH --> R-CN
    • 1)TsCl, pyridine
    • 2)NaCN
  12. R-CN + 1)LiAlH4 2)H2O->
    R-CH2-NH2
  13. R-CN --> R-CH2-NH2
    • 1)LiAlH4
    • 2)H2O
  14. R-NO2 + Sn, conc HCl, heat->
    R-NH2 (primary amine)
  15. Hofmann's Rearrangement
    primary amide + X2 + 4NaOH + heat-> primary amine + 2NaX + 2H2O + NaCO3
  16. primary amide + X2 + 4NaOH + heat->
    primary amine + 2NaX + 2H2O + NaCO3
  17. acid chloride + NH3->
    primary amide
  18. acid chloride + primary amine->
    secondary amide
  19. acid chloride + secondary amine->
    tertiary amide
  20. acid chloride --> primary amide
    NH3
  21. acid chloride --> secondary amide
    primary amine
  22. acid chloride --> tertiary amide
    secondary amine
  23. amide + 1)LiAlH4 2)H2O->
    amine
  24. amide --> amine
    • 1)LiAlH4
    • 2)H2O
  25. aldehyde or ketone + amine->
    imine ((R)2-C=N-R)
  26. aldehyde or ketone --> imine ((R)2-C=N-R)
    amine (NH3 or primary)
  27. imine + 1)LiAlH4 2)H2O->
    amine (primary or secondary)
  28. imine --> amine (primary or secondary)
    • 1)LiAlH4
    • 2)H2O
  29. aldehyde or ketone + 1)secondary amine 2)Na(CH3COO)2BH->
    tertiary amine
  30. aldehyde or ketone --> tertiary amine
    • 1)secondary amine
    • 2)Na(CH3COO)2BH

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