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

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

Procedure: To this N,N-bis(3-chloropropyl)methylamine is added 166 ml of a 2.06 M solution of trimethylamine in acetonitrile. The resulting mixture is allowed to stand at a temperature of about 25° C. for a period of 21 hours during which time a white solid material crystallizes; the mixture is stirred for an additional 7-hour period, the solid crystalline material is recovered by filtration, washed with a small amount of acetonitrile, then with ether, and finally with hexane, the washings being collected separately. The washed crystalline material is dried in vacuo at 25° C. to give about 6.0 grams of bis(3-trimethylammoniopropyl)methylamine dichloride; the latter is dissolved in isopropanol, an equivalent amount of anhydrous hydrogen chloride is added, and the hydrochloride salt, which precipitates, is recovered by filtration and dried to give substantially pure bis(3-trimethylammoniopropyl)methylamine dichloride hydrochloride; m.p. 251°-253° C. a white solid material crystallizes the solid crystalline material is recovered by filtration washed with a small amount of acetonitrile with ether, and finally with hexane, the washings being collected separately The washed crystalline material is dried in vacuo at 25° C.

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

Procedure: To this N,N-bis(3-chloropropyl)methylamine is added 166 ml of a 2.06 M solution of trimethylamine in acetonitrile. The resulting mixture is allowed to stand at a temperature of about 25° C. for a period of 21 hours during which time a white solid material crystallizes; the mixture is stirred for an additional 7-hour period, the solid crystalline material is recovered by filtration, washed with a small amount of acetonitrile, then with ether, and finally with hexane, the washings being collected separately. The washed crystalline material is dried in vacuo at 25° C. to give about 6.0 grams of bis(3-trimethylammoniopropyl) methylamine dichloride; the latter is dissolved in isopropanol, an equivalent amount of anhydrous hydrogen chloride is added, and the hydrochloride salt, which precipitates, is recovered by filtration and dried to give substantially pure bis(3-trimethylammoniopropyl)methylamine dichloride hydrochloride; m.p. 251-253° C. a white solid material crystallizes the solid crystalline material is recovered by filtration washed with a small amount of acetonitrile with ether, and finally with hexane, the washings being collected separately The washed crystalline material is 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: To this N,N-bis(3-chloropropyl)methylamine is added 166 ml of a 2.06 M solution of trimethylamine in acetonitrile. The resulting mixture is allowed to stand at a temperature of about 25° C. for a period of 21 hours during which time a white solid material crystallizes; the mixture is stirred for an additional 7-hour period, the solid crystalline material is recovered by filtration, washed with a small amount of acetonitrile, then with ether, and finally with hexane, the washings being collected separately. The washed crystalline material is dried in vacuo at 25° C. to give about 6.0 grams of bis(3-trimethylammoniopropyl) methylamine dichloride; the latter is dissolved in isopropanol, an equivalent amount of anhydrous hydrogen chloride is added, and the hydrochloride salt, which precipitates, is recovered by filtration and dried to give substantially pure bis(3-trimethylammoniopropyl)methylamine dichloride hydrochloride; m.p. 251°-253° C. a white solid material crystallizes the solid crystalline material is recovered by filtration washed with a small amount of acetonitrile with ether, and finally with hexane, the washings being collected separately The washed crystalline material is dried in vacuo at 25° C.

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

Procedure: To this N,N-bis(3-chloropropyl)methylamine is added 166 ml of a 2.06 M solution of trimethylamine in acetonitrile. The resulting mixture is allowed to stand at a temperature of about 25° C. for a period of 21 hours during which time a white solid material crystallizes; the mixture is stirred for an additional 7-hour period, the solid crystalline material is recovered by filtration, washed with a small amount of acetonitrile, then with ether, and finally with hexane, the washings being collected separately. The washed crystalline material is dried in vacuo at 25° C. to give about 6.0 grams of bis(3-trimethylammoniopropyl)methylamine dichloride; the latter is dissolved in isopropanol, an equivalent amount of anhydrous hydrogen chloride is added, and the hydrochloride salt, which precipitates, is recovered by filtration and dried to give substantially pure bis(3-trimethylammoniopropyl)methylamine dichloride hydrochloride; m.p. 251°-253° C. a white solid material crystallizes the solid crystalline material is recovered by filtration washed with a small amount of acetonitrile with ether, and finally with hexane, the washings being collected separately The washed crystalline material is dried in vacuo at 25° C.

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

Procedure: To this N,N-bis(3-chloropropyl)methylamine is added 166 ml of a 2.06 M solution of trimethylamine in acetonitrile. The resulting mixture is allowed to stand at a temperature of about 25° C. for a period of 21 hours during which time a white solid material crystallizes; the mixture is stirred for an additional 7-hour period, the solid crystalline material is recovered by filtration, washed with a small amount of acetonitrile, then with ether, and finally with hexane, the washings being collected separately. The washed crystalline material is dried in vacuo at 25° C. to give about 6.0 grams of bis(3-trimethylammoniopropyl) methylamine dichloride; the latter is dissolved in isopropanol, an equivalent amount of anhydrous hydrogen chloride is added, and the hydrochloride salt, which precipitates, is recovered by filtration and dried to give substantially pure bis(3-trimethylammoniopropyl)methylamine dichloride hydrochloride; m.p. 251-253° C. a white solid material crystallizes the solid crystalline material is recovered by filtration washed with a small amount of acetonitrile with ether, and finally with hexane, the washings being collected separately The washed crystalline material is 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.