Synthesis of N ‐methyl‐3‐aza[10] paracyclophane: A rigid analog of phenethylamine

The synthesis of N ‐methyl‐3‐aza[10]paracyclophane is reported which represents the first example of this ring system being formed via an acyloin reaction. This 3‐aza[10]paraeyclophane ring system behaves physiochemically inbetween the normal [9]‐ and [10]paracyclophane ring systems. Reductive desulfurization of N ‐methyl‐3‐aza[10]paracyclophane‐6‐ethylene thioketal in ethanol provides a small amount of the title compound and an unexpected, ring‐opened product, N ‐ethyl‐ N ‐methyl‐ p ‐heptylphenethylamine. A possible mechanism for the ring‐opening process is suggested.