3-chloro-N-(3-chloropropyl)-N-methylpropan-1-amine;hydrochloride

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

Procedure: A solution of about 60 grams of N,N-bis(3-hydroxypropyl)methylamine in 110 ml of chloroform is saturated, with cooling and stirring, with anhydrous hydrogen chloride gas. To the resulting two-phase liquid mixture is added, over a period of about 30 minutes at a temperature of 0-5° C., approximately 66 ml of thionyl chloride. The homogeneous solution thus obtained is allowed to stand at room temperature for a period of about 15 hours, the solution is then heated at reflux temperature for an additional two-hour period, and the chloroform is evaporated in vacuo from the light brown-colored reaction solution. The residual material is washed with ethanol, and is then crystallized from a mixture of 200 ml ethanol: 800 ml ether. The white crystalline product thus obtained is recovered by filtration, washed with three portions of ether, then with hexane, and dried in vacuo at 25° C. to give about 80 grams of N,N-bis(3-chloropropyl) methylamine hydrochloride; m.p. 86-88° C. with cooling The homogeneous solution thus obtained the solution is then heated at reflux temperature for an additional two-hour period the chloroform is evaporated in vacuo from the light brown-colored reaction solution The residual material is washed with ethanol is then crystallized from a mixture of 200 ml ethanol The white crystalline product thus obtained is recovered by filtration washed with three portions of ether with hexane, and dried in vacuo at 25° C.

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

Procedure: A solution of about 60 grams of N,N-bis(3-hydroxypropyl)methylamine in 110 ml of chloroform is saturated, with cooling and stirring, with anhydrous hydrogen chloride gas. To the resulting two-phase liquid mixture is added, over a period of about 30 minutes at a temperature of 0-5° C., approximately 66 ml of thionyl chloride. The homogeneous solution thus obtained is allowed to stand at room temperature for a period of about 15 hours, the solution is then heated at reflux temperature for an additional two-hour period, and the chloroform is evaporated in vacuo from the light brown-colored reaction solution. The residual material is washed with ethanol, and is then crystallized from a mixture of 200 ml ethanol: 800 ml ether. The white crystalline product thus obtained is recovered by filtration, washed with three portions of ether, then with hexane, and dried in vacuo at 25° C. to give about 80 grams of N,N-bis(3-chloropropyl) methylamine hydrochloride; m.p. 86-88° C. with cooling The homogeneous solution thus obtained the solution is then heated at reflux temperature for an additional two-hour period the chloroform is evaporated in vacuo from the light brown-colored reaction solution The residual material is washed with ethanol is then crystallized from a mixture of 200 ml ethanol The white crystalline product thus obtained is recovered by filtration washed with three portions of ether with hexane, and dried in vacuo at 25° C.

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

Procedure: In accordance with the present invention, N,N-bis(3-chloropropyl)methylamine hydrochloride is reacted with a base, as for example an alkali metal carbonate such as sodium carbonate, thereby forming the free tertiary amine, N,N,-bis(3-chloropropyl) methylamine, and this tertiary amine is reacted with trimethylamine to form a mixture of the diquaternary salt, bis(3-trimethylammoniopropyl) methylamine dichloride, and the desired monoquaternary salt, 3-[N-(3-chloropropyl)methylamino]-N,N,N-trimethylpropan-1-aminium chloride; this monoquaternary salt is converted to the corresponding 3-[N-(3-chloropropyl) methylamino]-N,N,N-trimethyl-propan-1-aminium chloride hydrochloride by reaction with hydrochloric acid.

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

Procedure: A solution of about 60 grams of N,N-bis(3-hydroxypropyl)methylamine in 110 ml of chloroform is saturated, with cooling and stirring, with anhydrous hydrogen chloride gas. To the resulting two-phase liquid mixture is added, over a period of about 30 minutes at a temperature of 0-5° C., approximately 66 ml of thionyl chloride. The homogeneous solution thus obtained is allowed to stand at room temperature for a period of about 15 hours, the solution is then heated at reflux temperature for an additional two-hour period, and the chloroform is evaporated in vacuo from the light brown-colored reaction solution. The residual material is washed with ethanol, and is then crystallized from a mixture of 200 ml ethanol: 800 ml ether. The white crystalline product thus obtained is recovered by filtration, washed with three portions of ether, then with hexane, and dried in vacuo at 25° C. to give about 80 grams of N,N-bis(3-chloropropyl) methylamine hydrochloride; m.p. 86-88° C. with cooling The homogeneous solution thus obtained the solution is then heated at reflux temperature for an additional two-hour period the chloroform is evaporated in vacuo from the light brown-colored reaction solution The residual material is washed with ethanol is then crystallized from a mixture of 200 ml ethanol The white crystalline product thus obtained is recovered by filtration washed with three portions of ether with hexane, and dried in vacuo at 25° C.

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

Procedure: In accordance with the present invention, N,N-bis(3-chloropropyl)methylamine hydrochloride is reacted with a base, as for example an alkali metal carbonate such as sodium carbonate, thereby forming the free tertiary amine, N,N,-bis(3-chloropropyl) methylamine, and this tertiary amine is reacted with trimethylamine to form a mixture of the diquaternary salt, bis(3-trimethylammoniopropyl) methylamine dichloride, and the desired monoquaternary salt, 3-[N-(3-chloropropyl)methylamino]-N,N,N-trimethylpropan-1-aminium chloride; this monoquaternary salt is converted to the corresponding 3-[N-(3-chloropropyl) methylamino]-N,N,N-trimethyl-propan-1-aminium chloride hydrochloride by reaction with hydrochloric acid.