N,N'-dibutylethane-1,2-diamine

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

Procedure: To 10 g (69.0 mmoles) of 40 percent glyoxal and 200 ml of methanol is rapidly added 11.9 g (69.0 mmoles) of N,N'-di(n-butyl)ethylenediamine. The solution is rapidly brought to reflux and heating is maintained for 5 minutes. The dark brown solution is then allowed to cool to room temperature at which time fine white crystals precipitate from the brown oil. The oil is diluted with 100 ml of 1,4-dioxane and the solid is removed by filtration. The dioxane solution is concentrated under aspirator vacuum and distilled in a short path distillation apparatus to give 4.5 g of 1,4-di(n-butyl)piperazin-2-one in the form of a brown oil (31 percent yield). to reflux heating is maintained for 5 minutes the solid is removed by filtration The dioxane solution is concentrated under aspirator vacuum distilled in a short path distillation apparatus

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

Procedure: To 10 g (69.0 mmoles) of 40 percent glyoxal and 200 ml of methanol is rapidly added 11.9 g (69.0 mmoles) of N,N'-di(n-butyl)ethylenediamine. The solution is rapidly brought to reflux and heating is maintained for 5 minutes. The dark brown solution is then allowed to cool to room temperature at which time fine white crystals precipitate from the brown oil. The oil is diluted with 100 ml of 1,4-dioxane and the solid is removed by filtration. The dioxane solution is concentrated under aspirator vacuum and distilled in a short path distillation apparatus to give 4.5 g of 1,4-di(n-butyl)piperazin-2-one in the form of a brown oil (31 percent yield). to reflux heating is maintained for 5 minutes the solid is removed by filtration The dioxane solution is concentrated under aspirator vacuum distilled in a short path distillation apparatus

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

Procedure: To 10 g (69.0 mmoles) of 40 percent glyoxal and 200 ml of methanol is rapidly added 11.9 g (69.0 mmoles) of N,N'-di(n-butyl)ethylenediamine. The solution is rapidly brought to reflux and heating is maintained for 5 minutes. The dark brown solution is then allowed to cool to room temperature at which time fine white crystals precipitate from the brown oil. The oil is diluted with 100 ml of 1,4-dioxane and the solid is removed by filtration. The dioxane solution is concentrated under aspirator vacuum and distilled in a short path distillation apparatus to give 4.5 g of 1,4-di(n-butyl)piperazin-2-one in the form of a brown oil (31 percent yield). to reflux heating is maintained for 5 minutes the solid is removed by filtration The dioxane solution is concentrated under aspirator vacuum distilled in a short path distillation apparatus

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

Procedure: Several secondary diamine adducts of cobalt(II) acetylacetonate were prepared by adding 1.04 grams (4 millimoles) of cobalt acetylacetonate into a 50 ml two-necked flask. There was then added 30 ml of freshly distilled toluene along with a stir bar. The mixture was heated and residual water bound to the cobalt acetylacetonate was azotropically removed. When the distillation temperature reached 110° C., heating of the mixture was discontinued. There was then added 0.76 grams (4.4 millimoles) of N,N'-dibutylethylenediamine when the refluxing had subsided. The solution was stirred for one hour and allowed to cool. The product was crystallized from the solution after removal of some of the solvent by rotoevaporation. Recrystallization was effected from a hexane/methylenechloride mixture at -20° C. The same procedure was repeated except that in place of N,N'-di-t-butylethylenediamine there was added N,N'-t-N-butylethylenediamine. The following results were obtained: The mixture was heated was azotropically removed reached 110° C. heating of the mixture to cool The product was crystallized from the solution after removal of some of the solvent by rotoevaporation Recrystallization was effected from a hexane/methylenechloride mixture at -20° C there was added N,N'-t-N-butylethylenediamine The following results were obtained

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

Procedure: Several secondary diamine adducts of cobalt(II) acetylacetonate were prepared by adding 1.04 grams (4 millimoles) of cobalt acetylacetonate into a 50 ml two-necked flask. There was then added 30 ml of freshly distilled toluene along with a stir bar. The mixture was heated and residual water bound to the cobalt acetylacetonate was azotropically removed. When the distillation temperature reached 110° C., heating of the mixture was discontinued. There was then added 0.76 grams (4.4 millimoles) of N,N'-dibutylethylenediamine when the refluxing had subsided. The solution was stirred for one hour and allowed to cool. The product was crystallized from the solution after removal of some of the solvent by rotoevaporation. Recrystallization was effected from a hexane/methylenechloride mixture at -20° C. The same procedure was repeated except that in place of N,N'-di-t-butylethylenediamine there was added N,N'-t-N-butylethylenediamine. The following results were obtained: The mixture was heated was azotropically removed reached 110° C. heating of the mixture to cool The product was crystallized from the solution after removal of some of the solvent by rotoevaporation Recrystallization was effected from a hexane/methylenechloride mixture at -20° C there was added N,N'-t-N-butylethylenediamine The following results were obtained