3-[3-hydroxypropyl(methyl)amino]propan-1-ol

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: To this aqueous N-(3-hydroxypropyl)methylamine solution is added a second 249.5 g portion of 3-chloro-1-propanol, and the resulting mixture is heated under reflux at a temperature of approximately 105° C. for a period of about 5 hours, during which time about 195 grams of a 50% aqueous sodium hydroxide solution is added slowly at a rate sufficient to maintain the pH between about 8 and 9. The reaction mixture is cooled to room temperature, filtered, and the filtered aqueous solution is extracted with three 500 ml-portions of n-butanol. The butanol extracts are combined, evaporated to a small volume in vacuo, and the residual slurry is triturated with 300 ml of ethyl ether. The resulting ethereal slurry is filtered, thereby removing insoluble inorganic solid material, and the latter is washed with 100 ml of ethyl ether. The ether solution and washings are combined, the ether is evaporated therefrom in vacuo, and the residual oil is distilled in vacuo to give about 123 grams of N,N-bis(3-hydroxypropyl)methylamine; b.p. 110° C. at 150 microns pressure. the resulting mixture is heated is added slowly at a rate sufficient to maintain the pH between about 8 and 9 filtered the filtered aqueous solution is extracted with three 500 ml-portions of n-butanol evaporated to a small volume in vacuo the residual slurry is triturated with 300 ml of ethyl ether The resulting ethereal slurry is filtered removing insoluble inorganic solid material, and the latter is washed with 100 ml of ethyl ether the ether is evaporated in vacuo, and the residual oil is distilled in vacuo

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: To this aqueous N-(3-hydroxypropyl)methylamine solution is added a second 249.5 g portion of 3-chloro-1-propanol, and the resulting mixture is heated under reflux at a temperature of approximately 105° C. for a period of about 5 hours, during which time about 195 grams of a 50% aqueous sodium hydroxide solution is added slowly at a rate sufficient to maintain the pH between about 8 and 9. The reaction mixture is cooled to room temperature, filtered, and the filtered aqueous solution is extracted with three 500 ml-portions of n-butanol. The butanol extracts are combined, evaporated to a small volume in vacuo, and the residual slurry is triturated with 300 ml of ethyl ether. The resulting ethereal slurry is filtered, thereby removing insoluble inorganic solid material, and the latter is washed with 100 ml of ethyl ether. The ether solution and washings are combined, the ether is evaporated therefrom in vacuo, and the residual oil is distilled in vacuo to give about 123 grams of N,N-bis(3-hydroxypropyl)methylamine; b.p. 110° C. at 150 microns pressure. the resulting mixture is heated is added slowly at a rate sufficient to maintain the pH between about 8 and 9 filtered the filtered aqueous solution is extracted with three 500 ml-portions of n-butanol evaporated to a small volume in vacuo the residual slurry is triturated with 300 ml of ethyl ether The resulting ethereal slurry is filtered removing insoluble inorganic solid material, and the latter is washed with 100 ml of ethyl ether the ether is evaporated in vacuo, and the residual oil is distilled in vacuo