The intermediate (1) was reductively aminated with aniline using Zn dust in acetic acid, to afford anilino-amide (2).
The reaction conditions are: PhNH2, Zn, AcOH, rt 12h, reflux 3h
Usually, they condense the ketone with PhNH2 by refluxing it in toluene and azeotropically removing the H2O while the imine forms. Then the imine is reduced with NaBH4 in MeOH.
In Synthesis (1991) p 1043 - 1045, they do those 2 steps in one. In this article, they condense PhNH2 with cyclohexanone and reduce it to afford N-cyclohexylaniline.
Procedure:
"Into a 500 mL three necked flask equipped with mechanical stirrer, reflux condenser and thermometer are combined AcOH (250 ml), H2O (25 ml), activated Zn dust (78.45 g, 1.20 mol), aniline (27.94 g, 27.3 ml, 0.30 mol) and cyclohexanone (29.44 g, 31.3 ml, 0.30 mol). Stirring is initiated and after a modestly exothermic reaction (ca. 30 min), the mixture is heated on a water bath (2h, 60 – 70 °C). After cooling, the mixture is diluted with MeOH (100 ml), and filtered with a sinter funnel. The solids are washed with MeOH (2 x 100 mL), and the combined filtrates are concentrated at 50 °C with a rotary evaporator. Crushed ice (100 g), and DCM (200 mL), are added to the residue with shaking, followed with excess 25 % NH4OH until pH is ca. 10. The organic layer is separated, the aqueous layer is extracted with DCM (2 x 100 mL), and the combined extracts dried (MgSO4). The residue is distilled to afford pure N-cyclohexylaniline; yield: 47.4 g (90 %)"
Just let the reaction sit 12 hours at room temperature,
and then heat it to 60 - 70 °C for 3 hours.