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Reductive amination

3 real reactions from the literature, on aromatic aldehydes, six-membered cyclic ketones and aryl ketones. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Reductive amination: 2,3-dimethoxybenzaldehyde (an aromatic aldehyde) with CH3NH2, H2 (45 psi), Raney nickel; aq. CH3CH2OH, 70 °C gives 1-(2,3-dimethoxyphenyl)-N-methylmethanamine (the secondary amine).

  2. Reductive amination: cyclohexanone (a six-membered cyclic ketone) and dimethylamine (a secondary amine) with Me2NH·HCl, NaBH3CN, KOH; CH3OH gives N,N-dimethylcyclohexylamine (the tertiary amine).

  3. Reductive amination: acetophenone (an aryl ketone) with H2, Ra(Ni) (3500 - 5000 psi); NH3, 150 °C gives 1-phenylethylamine (the primary amine).