N-Hexyl-2-methyl-4-methoxyaniline and N-Methyl-n-(4-chlorophenyl)aniline  could be produced through many synthetic methods.

A. N-Hexyl-2-methyl-4-methoxyaniline. A 250-mL, round-bottomed flask equipped with a magnetic stirbar and a rubber septum is flame-dried and allowed to cool to room temperature under an argon purge. The septum is removed and the flask is charged with tris(dibenzylideneacetone)dipalladium(0) (114 mg, 0.125 mmol, 0.5 mol% Pd), (±)-BINAP (233 mg, 0.375 mmol, 0.75 mol%), and sodium tert-butoxide (NaOtBu) (6.73 g, 70.0 mmol, 1.4 equiv). The septum is again placed on the flask, and the flask is purged with argon for 5 min. (50 mL) is added and stirring is started. The flask is charged with 4-bromo- (10.0 g, 50.0 mmol, 1.0 equiv), n-hexylamine (7.9 mL, 60.0 mmol, 1.2 equiv), and additional toluene (50 mL). The resulting dark red mixture is placed in an oil bath that is heated to 80°C with stirring until the aryl bromide has been completely consumed as judged by GC analysis (18-23 hr). The mixture is removed from the oil bath, allowed to cool to room temperature, then poured into a separatory funnel. The reaction flask is rinsed with ether (2 × 50 mL), brine (100 mL), deionized water (20 mL), and again with ether (50 mL). All rinses are added to the separatory funnel, the funnel is shaken, and the layers are separated. The aqueous layer is extracted with ether (50 mL), and the combined organic extracts are dried over anhydrous magnesium sulfate . The mixture is filtered; the magnesium sulfate is washed with ether (50 mL), filtered, and the organic solution is concentrated under reduced pressure to give the crude product as a brown oil. This oil is then distilled (bulb-to-bulb, bp 92°C at 0.001 mm) to afford 10.35 g (94%) of the desired product as a pale yellow oil. A small amount of viscous material remains in the distillation flask following the distillation.

B. N-Methyl-N-(4-chlorophenyl)aniline (CAS NO.: ). A 250-mL, three-necked, round-bottomed flask equipped with a reflux condenser, magnetic stirbar, one glass stopper, and rubber septa, covering the condenser and the remaining neck of the flask, is flame-dried and allowed to cool to room temperature under an argon purge. The septum is removed and the flask is charged with palladium acetate (337 mg, 1.5 mmol, 3.0 mol% Pd) and (±)-BINAP (1.4 g, 2.25 mmol, 4.5 mol%). The septum is again placed on the flask, and the flask is purged with argon for 5 min. (THF) (50 mL) is added and the mixture stirred at room temperature for 10 min until a peach-colored suspension forms. The flask is charged with 4-chlorophenyl trifluoromethanesulfonate (13.0 g, 50.0 mmol, 1.0 equiv), and N-methylaniline (6.5 mL, 60.0 mmol, 1.2 equiv). The septum is removed from the flask, and cesium carbonate (Cs₂CO₃) (22.8 g, 70.0 mmol, 1.4 equiv) is added under a flow of argon. The septum is again placed over the flask, and the flask is purged with argon for 30 seconds. Additional THF (50 mL) is added, the reaction mixture is immersed in a 70°C oil bath so that the level of the oil is even with the level of solvent in the flask and stirring is begun. The internal temperature of the reaction is monitored using a thermocouple and is found to be 60°C (±1°C). The mixture is stirred at this temperature until all the starting triflate has been consumed as judged by GC analysis (23-45 hr). The mixture is removed from the oil bath and allowed to cool to room temperature. Ether (100 mL) and hexanes (50 mL) are added to the flask and the solution formed is filtered through Celite. The flask is rinsed with ether (3 × 50 mL) and the rinses are filtered through Celite. The organic extracts are combined and concentrated under reduced pressure, and 1/1 (v/v) hexanes/ether (200 mL) is added. A yellow precipitate forms, and the mixture is filtered through a 1.5-inch deep plug of silica gel on a 3"-diameter type D fritted funnel. The flask is rinsed with 1/1 (v/v) hexanes/ether (2 × 100 mL), and the rinses are filtered through the plug of silica gel. The organic solution is concentrated under reduced pressure to give a light brown oil. The material is distilled (bulb to bulb, 0.002 mm). A low boiling fraction (bp 58-70°C) is collected; the distillation is stopped and the low boiling material is rinsed out of the receiver bulb. The distillation is resumed (bulb-to-bulb, bp 84°C at 0.002 mm) to give a yellow solid that melts at room temperature to give 9.72 g (90%) of the desired product as a pale yellow oil.