Acetic Acid → (R)-alpha-Methyl-N-(2-ethylcyclohexylidene)-benzenemethanamine

Participants

Reaction Steps

A solution of 2-ethylcyclohexanone (6.92 mol, 873 g), (R)-α-methylbenzylamine (6.92 mol, 839 g), and 19.6 mL of acetic acid were refluxed for 12 hours under nitrogen in 2 L of toluene with azeotropic removal of water. The toluene was removed on a rotary evaporator and the product was divided into two portions. The unreacted 2-ethylcyclohexanone was distilled through a short path (bp 30° C., <10 mm), and the remainder of the product was then distilled through a 5" vacuum jacketed Vigreux column affording first a low melting solid (bp 80°-90° C. 23 mm), and then the product (bp 128°-133° C. 21.0 mm, 1.303 kg from both distillations combined, 5.68 mol, 82%).

Provenance & Evidence