N-methyl-N-octyloctan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 mL, round-bottomed flask equipped with air condensers and magnetic stirring was charged N-methyldioctylamine (201.83 grams, 0.790 moles), 1-bromo-4-chlorobutane (135.517 grams, 0.790 moles) and methanol (250 mL). The reaction was maintained at 68° C. for 48 hours. The reaction was cooled to room temperature. Solvent was removed by rotary evaporation until a thick oil remained. Solvent removal was continued under high vacuum at 50° C., yielding 333.53 grams of a thick brown oil. To a 500 mL, round-bottomed flask equipped with air condensers The reaction was cooled to room temperature Solvent was removed by rotary evaporation until a thick oil Solvent removal was continued under high vacuum at 50° C.

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A one-liter, 3-necked, round-bottomed flask equipped with air condensers and a magnetic stirring plate was charged with N,N-dioctylmethylamine (202.48 grams, 0.79 moles), 1-bromo-3-chloropropane (124.8 grams, 0.79 moles) and methanol (250 mL). Reaction was maintained at 65° C. for two days. Methanol was removed by rotary evaporation under reduced pressure to yield an oil. To the oil was added ethylmethylketone (50 mL) and hexane (200 mL) causing a white solid to slowly form. The solvent was decanted from the mixture. The remaining solid was washed with hexane (50 mL) two times. The solid was placed in a vacuum oven at 35° C. for 24 hours. Yield 259 grams of a waxy solid (0.625 moles, 79%). A one-liter, 3-necked, round-bottomed flask equipped with air condensers Reaction Methanol was removed by rotary evaporation under reduced pressure to yield an oil to slowly form The solvent was decanted from the mixture The remaining solid was washed with hexane (50 mL) two times

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

Procedure: By essentially the procedure of Example 1, a tube was charged with 40 g of methyldioctylamine and 1.0 g of CuCl2. 2H2O. The reaction was run at 109°-120° C. for 25 min while oxygen (0.2 mole) was injected incrementally at 160-275 psi. GC/MS analysis showed a 72.0% conversion of methyldioctylamine and a 4.5% yield of dioctylformamide.

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

Procedure: Following the general procedure of Example 1, 5.0 g. of N-methyl-N,N-dioctylamine was reacted with methyl bromide in diethyl ether to provide, after crystallization from diethyl ether, 6.89 g. of N,N-dimethyl-N,N-dioctylammonium bromide. to provide after crystallization from diethyl ether, 6.89 g

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Following the general procedure of Example 1, 5.0 g. of N-methyl-N,N-dioctylamine was reacted with methyl bromide in diethyl ether to provide, after crystallization from diethyl ether, 6.89 g. of N,N-dimethyl-N,N-dioctylammonium bromide. to provide after crystallization from diethyl ether, 6.89 g

Conditions: temp:68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 mL, round-bottomed flask equipped with air condensers and magnetic stirring was charged N-methyldioctylamine (201.83 grams, 0.790 moles), 1-bromo-4-chlorobutane (135.517 grams, 0.790 moles) and methanol (250 mL). The reaction was maintained at 68° C. for 48 hours. The reaction was cooled to room temperature. Solvent was removed by rotary evaporation until a thick oil remained. Solvent removal was continued under high vacuum at 50° C., yielding 333.53 grams of a thick, brown oil. To a 500 mL, round-bottomed flask equipped with air condensers The reaction was cooled to room temperature Solvent was removed by rotary evaporation until a thick oil Solvent removal was continued under high vacuum at 50° C. yielding 333.53 grams of a thick, brown oil

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A one-liter, 3-necked, round-bottomed flask equipped with air condensers and a magnetic stirring plate was charged with N,N-dioctylmethylamine (202.48 grams, 0.79 moles), 1-bromo-3-chloropropane (124.8 grams, 0.79 moles) and methanol (250 mL). Reaction was maintained at 65° C. for two days. Methanol was removed by rotary evaporation under reduced pressure to yield an oil. To the oil was added ethylmethylketone (50 mL) and hexane (200 mL) causing a white solid to slowly form. The solvent was decanted from the mixture. The remaining solid was washed with hexane (50 mL) two times. The solid was placed in a vacuum oven at 35° C. for 24 hours. Yield 259 grams of a waxy solid (0.625 moles, 79%). A one-liter, 3-necked, round-bottomed flask equipped with air condensers Reaction Methanol was removed by rotary evaporation under reduced pressure to yield an oil to slowly form The solvent was decanted from the mixture The remaining solid was washed with hexane (50 mL) two times

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

Procedure: Initially a hydroxyethyl quat was made by reacting 100 grams of dioctyl methyl amine with 42 mLs of 2-chloroethanol in 200 grams of methylethyl ketone solvent at reflux for 5 hours to obtain a methylethyl ketone solution of dioctyl methyl hydroxyethyl ammonium chloride. To this was added dropwise, 59.04 grams of glutaryl dichloride over a 1 hour period while sparging the mixture with nitrogen. This was held at reflux (90° C.) for 30 minutes to give a brown solution of di(dioctyl methyl ammonium ethyl)glutarate dichloride which could be recovered by evaporation of the methylethyl ketone under vacuum. at reflux for 5 hours

Conditions: temp:68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 mL, round-bottomed flask equipped with air condensers and magnetic stirring was charged N-methyldioctylamine (201.83 grams, 0.790 moles), 1-bromo-4-chlorobutane (135.517 grams, 0.790 moles) and methanol (250 mL). The reaction was maintained at 68° C. for 48 hours. The reaction was cooled to room temperature. Solvent was removed by rotary evaporation until a thick oil remained. Solvent removal was continued under high vacuum at 50° C., yielding 333.53 grams of a thick brown oil. To a 500 mL, round-bottomed flask equipped with air condensers The reaction was cooled to room temperature Solvent was removed by rotary evaporation until a thick oil Solvent removal was continued under high vacuum at 50° C.

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A one-liter, 3-necked, round-bottomed flask equipped with air condensers and a magnetic stirring plate was charged with N,N-dioctylmethylamine (202.48 grams, 0.79 moles), 1-bromo-3-chloropropane (124.8 grams, 0.79 moles) and methanol (250 mL). Reaction was maintained at 65° C. for two days. Methanol was removed by rotary evaporation under reduced pressure to yield an oil. To the oil was added ethylmethylketone (50 mL) and hexane (200 mL) causing a white solid to slowly form. The solvent was decanted from the mixture. The remaining solid was washed with hexane (50 mL) two times. The solid was placed in a vacuum oven at 35° C. for 24 hours. Yield 259 grams of a waxy solid (0.625 moles, 79%). A one-liter, 3-necked, round-bottomed flask equipped with air condensers Reaction Methanol was removed by rotary evaporation under reduced pressure to yield an oil to slowly form The solvent was decanted from the mixture The remaining solid was washed with hexane (50 mL) two times