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Ch. 19 - Amines
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Capitolo 19, Problema 42d

Using any necessary reagents, show how you would accomplish the following syntheses.
(d) Chemical reaction diagram showing the conversion of a cyclic ketone to a cyclic amine with an amine group.

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Step 1: Analyze the transformation. The starting material is a cyclic ketone (cyclooctanone), and the product is a cyclic amine (cyclooctylamine). This indicates that the ketone functional group needs to be converted into an amine group.
Step 2: Use reductive amination as the key reaction. Reductive amination involves the reaction of a ketone with ammonia (NH₃) or a primary amine in the presence of a reducing agent to form an amine.
Step 3: Add ammonia (NH₃) to the ketone. This will form an imine intermediate through a condensation reaction where water is eliminated. The imine has the general structure R₂C=NH.
Step 4: Reduce the imine intermediate to the amine. Use a reducing agent such as sodium cyanoborohydride (NaBH₃CN) or hydrogen gas (H₂) with a metal catalyst (e.g., Pd/C) to selectively reduce the imine to the amine without affecting other parts of the molecule.
Step 5: Confirm the product structure. The final product should be cyclooctylamine, where the ketone group has been successfully replaced with an amine group.

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