N-ethyl-2,6-dimethylaniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-ethyl-2,6-dimethylaniline (5.9 g, 39.6 mmol) was added to a stirred solution of cyanogen bromide (2.1 g, 19.8 mmol) in toluene (50 mL). The reaction mixture was allowed to react overnight at room temperature during which a solid formed. A small temperature rise to 30° C. was observed. The suspension was filtered and the residue was washed with toluene (3×25 mL). The combined filtrates were evaporated to dryness by rotatory evaporation and the resulting residue was purified by Kugelrohr distillation (0.2 mbar, 110-125° C.) yielding a brown oil. Yield: 3.09 g (90%). The residue (N-ethyl-2,6-dimethylaniline hydrobromide) of the filtration step was used in the following synthetic step. to react overnight at room temperature during which a solid formed to 30° C. The suspension was filtered the residue was washed with toluene (3×25 mL) The combined filtrates were evaporated to dryness by rotatory evaporation the resulting residue was purified by Kugelrohr distillation (0.2 mbar, 110-125° C.) yielding a brown oil The residue (N-ethyl-2,6-dimethylaniline hydrobromide) of the filtration step

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium borohydride (19.0 g, 0.5 mol) was added in small portions to a stirred solution of N-ethylidene-2,6-dimethylaniline (36.3 g, 0.247 mol) in THF (150 mL) and methanol (150 mL). The reaction was exothermic and a water/ice bath was used to cool the mixture. After addition of sodium borohydride, the bath was removed and the mixture was allowed to react for another 30 min. Then, water (150 mL) was added to the reaction mixture, while stirring and cooling the mixture with a water/ice bath. The volatiles were removed in vacuo, the aqueous layer extracted with dichloromethane (3×150 mL) and the combined organic layers were dried with sodium sulfate. Filtration and rotatory vaporation of the volatiles yielded the desired product. Yield: 36.4 g (99%). a water/ice bath was used to cool the mixture the bath was removed to react for another 30 min cooling the mixture with a water/ice bath The volatiles were removed in vacuo the aqueous layer extracted with dichloromethane (3×150 mL) the combined organic layers were dried with sodium sulfate Filtration and rotatory vaporation of the volatiles

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-ethyl-2,6-dimethylaniline (5.9 g, 39.6 mmol) was added to a stirred solution of cyanogen bromide (2.1 g, 19.8 mmol) in toluene (50 mL). The reaction mixture was allowed to react overnight at room temperature during which a solid formed. A small temperature rise to 30° C. was observed. The suspension was filtered and the residue was washed with toluene (3×25 mL). The combined filtrates were evaporated to dryness by rotatory evaporation and the resulting residue was purified by Kugelrohr distillation (0.2 mbar, 110-125° C.) yielding a brown oil. Yield: 3.09 g (90%). The residue (N-ethyl-2,6-dimethylaniline hydrobromide) of the filtration step was used in the following synthetic step. to react overnight at room temperature during which a solid formed to 30° C. The suspension was filtered the residue was washed with toluene (3×25 mL) The combined filtrates were evaporated to dryness by rotatory evaporation the resulting residue was purified by Kugelrohr distillation (0.2 mbar, 110-125° C.) yielding a brown oil The residue (N-ethyl-2,6-dimethylaniline hydrobromide) of the filtration step

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium borohydride (19.0 g, 0.5 mol) was added in small portions to a stirred solution of N-ethylidene-2,6-dimethylaniline (36.3 g, 0.247 mol) in THF (150 mL) and methanol (150 mL). The reaction was exothermic and a water/ice bath was used to cool the mixture. After addition of sodium borohydride, the bath was removed and the mixture was allowed to react for another 30 min. Then, water (150 mL) was added to the reaction mixture, while stirring and cooling the mixture with a water/ice bath. The volatiles were removed in vacuo, the aqueous layer extracted with dichloromethane (3×150 mL) and the combined organic layers were dried with sodium sulfate. Filtration and rotatory vaporation of the volatiles yielded the desired product. Yield: 36.4 g (99%). a water/ice bath was used to cool the mixture the bath was removed to react for another 30 min cooling the mixture with a water/ice bath The volatiles were removed in vacuo the aqueous layer extracted with dichloromethane (3×150 mL) the combined organic layers were dried with sodium sulfate Filtration and rotatory vaporation of the volatiles