N-[3-(dimethylamino)propyl]dodecanamide

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 ml RB flask containing a solution of lauroyl chloride (19.38 g., 89 mM) in dry chloroform (200 ml) was cooled to 0° C. on an ice bath. A solution of N,N-dimethyl-1,3-propanediamine (10.40 g., 51 mM) and triethylamine (9.40 g., 93 mM) in dry chloroform (25ml) was added dropwise to the cold solution through an addition funnel, then allowed to warm to room temperature and stirred for 2 hours. The chloroform was removed under reduced pressure and the residue redissolved in an ethanol/water mixture (1:1) and neutralized with sodium bicarbonate, followed by extraction with chloroform (4×50 ml). The combined extracts were dried (MgSO4), concentrated, and the residue distilled under reduced pressure (bp 171° C., 10μ) to give 23.92 g. (68%) of the subject compound as an amber solid. to warm to room temperature The chloroform was removed under reduced pressure the residue redissolved in an ethanol/water mixture (1:1) followed by extraction with chloroform (4×50 ml) The combined extracts were dried (MgSO4) concentrated the residue distilled under reduced pressure (bp 171° C., 10μ) to give 23.92 g

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 ml RB flask containing a solution of lauroyl chloride (19.38 g., 89 mM) in dry chloroform (200 ml) was cooled to 0° C. on an ice bath. A solution of N,N-dimethyl-1,3-propanediamine (10.40 g., 51 mM) and triethylamine (9.40 g., 93 mM) in dry chloroform (25ml) was added dropwise to the cold solution through an addition funnel, then allowed to warm to room temperature and stirred for 2 hours. The chloroform was removed under reduced pressure and the residue redissolved in an ethanol/water mixture (1:1) and neutralized with sodium bicarbonate, followed by extraction with chloroform (4×50 ml). The combined extracts were dried (MgSO4), concentrated, and the residue distilled under reduced pressure (bp 171° C., 10μ) to give 23.92 g. (68%) of the subject compound as an amber solid. to warm to room temperature The chloroform was removed under reduced pressure the residue redissolved in an ethanol/water mixture (1:1) followed by extraction with chloroform (4×50 ml) The combined extracts were dried (MgSO4) concentrated the residue distilled under reduced pressure (bp 171° C., 10μ) to give 23.92 g

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 14.22 g (0.050 mol) portion of N-dodecanoyl-N′,N′-dimethyl-1,3-diaminopropane and 120 ml of diethyl ether were put into a flask, and 9.93 g (0.050 mol) of 2-phenylethyl chloroacetate was added thereto at 0 to 5° C. spending 5 minutes. The reaction mixture was further stirred at 25° C. for 24 hours, and disappearance of the most part of chloroacetate was confirmed by 1H-NMR. Next, the reaction mixture was slowly added dropwise to 600 ml of hexane which was ice-cooled and vigorously stirred, spending 10 minutes, to effect precipitation of the product as a white solid. Thereafter, in the same manner as described in Inventive Example 1, the title compound (to be referred to as betaine ester (11) hereinafter) was obtained as a white powder. Yield 20.10 g (0.0416 mol; yield 83.2%). cooled vigorously stirred spending 10 minutes precipitation of the product as a white solid

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 14.22 g (0.050 mol) portion of N-dodecanoyl-N′,N′-dimethyl-1,3-diaminopropane and 120 ml of diethyl ether were put into a flask, and 9.93 g (0.050 mol) of 2-phenylethyl chloroacetate was added thereto at 0 to 5° C. spending 5 minutes. The reaction mixture was further stirred at 25° C. for 24 hours, and disappearance of the most part of chloroacetate was confirmed by 1H-NMR. Next, the reaction mixture was slowly added dropwise to 600 ml of hexane which was ice-cooled and vigorously stirred, spending 10 minutes, to effect precipitation of the product as a white solid. Thereafter, in the same manner as described in Inventive Example 1, the title compound (to be referred to as betaine ester (11) hereinafter) was obtained as a white powder. Yield 20.10 g (0.0416 mol; yield 83.2%). cooled vigorously stirred spending 10 minutes precipitation of the product as a white solid

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 22.76 g (0.080 mol) portion of N-dodecanoyl-N′,N′-dimethyl-1,3-diaminopropane and 120 ml of diethyl ether were put into a flask, and 18.46 g (0.080 mol) of geranyl chloroacetate was added thereto at 25° C. spending 5 minutes. The reaction mixture was stirred at 25° C. for 24 hours, and disappearance of the most part of chloroacetate was confirmed by 1H-NMR. Next, the reaction mixture was slowly added dropwise to 600 ml of hexane which was ice-cooled and vigorously stirred, spending 10 minutes, to effect precipitation of the product as a white solid. Thereafter, in the same manner as described in Inventive Example 1, the title compound (to be referred to as betaine ester (3) hereinafter) was obtained as a light yellow viscous oil. Yield 38.50 g (0.0747 mol; yield 93.4%). cooled vigorously stirred spending 10 minutes precipitation of the product as a white solid

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 ml RB flask containing a solution of lauroyl chloride (19.38 g., 89 mM) in dry chloroform (200 ml) was cooled to 0° C. on an ice bath. A solution of N,N-dimethyl-1,3-propanediamine (10.40 g., 51 mM) and triethylamine (9.40 g., 93 mM) in dry chloroform (25ml) was added dropwise to the cold solution through an addition funnel, then allowed to warm to room temperature and stirred for 2 hours. The chloroform was removed under reduced pressure and the residue redissolved in an ethanol/water mixture (1:1) and neutralized with sodium bicarbonate, followed by extraction with chloroform (4×50 ml). The combined extracts were dried (MgSO4), concentrated, and the residue distilled under reduced pressure (bp 171° C., 10μ) to give 23.92 g. (68%) of the subject compound as an amber solid. to warm to room temperature The chloroform was removed under reduced pressure the residue redissolved in an ethanol/water mixture (1:1) followed by extraction with chloroform (4×50 ml) The combined extracts were dried (MgSO4) concentrated the residue distilled under reduced pressure (bp 171° C., 10μ) to give 23.92 g

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 ml RB flask containing a solution of lauroyl chloride (19.38 g., 89 mM) in dry chloroform (200 ml) was cooled to 0° C. on an ice bath. A solution of N,N-dimethyl-1,3-propanediamine (10.40 g., 51 mM) and triethylamine (9.40 g., 93 mM) in dry chloroform (25ml) was added dropwise to the cold solution through an addition funnel, then allowed to warm to room temperature and stirred for 2 hours. The chloroform was removed under reduced pressure and the residue redissolved in an ethanol/water mixture (1:1) and neutralized with sodium bicarbonate, followed by extraction with chloroform (4×50 ml). The combined extracts were dried (MgSO4), concentrated, and the residue distilled under reduced pressure (bp 171° C., 10μ) to give 23.92 g. (68%) of the subject compound as an amber solid. to warm to room temperature The chloroform was removed under reduced pressure the residue redissolved in an ethanol/water mixture (1:1) followed by extraction with chloroform (4×50 ml) The combined extracts were dried (MgSO4) concentrated the residue distilled under reduced pressure (bp 171° C., 10μ) to give 23.92 g

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

Procedure: 0.036 moles (10.3 g) N-(3-dimethylaminopropyl)-lauramide and 25 ml acetone were placed in a 100 ml round bottom flask. 0.036 moles (3.4 ml) dimethylsulfate was added slowly to the flask, a condenser attached, and the reaction mixture refluxed for two hours. After cooling, the product crystallized out of the acetone, was filtered off, and recrystallized from acetone to a constant melting point. Melting point 98.5°-100° C. the reaction mixture refluxed for two hours After cooling the product crystallized out of the acetone was filtered off recrystallized from acetone to

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

Procedure: 0.036 moles (10.3 g) N-(3-dimethylaminopropyl)-lauramide and 25 ml acetone were placed in a 100 ml round bottom flask. 0.036 moles (3.4 ml) dimethylsulfate was added slowly to the flask, a condenser attached, and the reaction mixture refluxed for two hours. After cooling, the product crystallized out of the acetone, was filtered off, and recrystallized from acetone to a constant melting point. Melting point 98.5°-100° C. the reaction mixture refluxed for two hours After cooling the product crystallized out of the acetone was filtered off recrystallized from acetone to

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

Procedure: 0.036 moles (10.3 g) N-(3-dimethylaminopropyl)-lauramide and 25 ml acetone were placed in a 100 ml round bottom flask. 0.036 moles (3.4 ml) dimethylsulfate was added slowly to the flask, a condenser attached, and the reaction mixture refluxed for two hours. After cooling, the product crystallized out of the acetone, was filtered off, and recrystallized from acetone to a constant melting point. Melting point 98.5°-100° C. the reaction mixture refluxed for two hours After cooling the product crystallized out of the acetone was filtered off recrystallized from acetone to

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 ml RB flask containing a solution of lauroyl chloride (19.38 g., 89 mM) in dry chloroform (200 ml) was cooled to 0° C. on an ice bath. A solution of N,N-dimethyl-1,3-propanediamine (10.40 g., 51 mM) and triethylamine (9.40 g., 93 mM) in dry chloroform (25 ml) was added dropwise to the cold solution through an addition funnel, then allowed to warm to room temperature and stirred for 2 hours. The chloroform was removed under reduced pressure and the residue redissolved in an ethanol/water mixture (1:1) and neutralized with sodium bicarbonate, followed by extraction with chloroform (4×50 ml). The combined extracts were dried (MgSO4), concentrated, and the residue distilled under reduced pressure (bp 171° C., 10 μ) to give 23.92 g. (68%) of the subject compound as an amber solid. to warm to room temperature The chloroform was removed under reduced pressure the residue redissolved in an ethanol/water mixture (1:1) followed by extraction with chloroform (4×50 ml) The combined extracts were dried (MgSO4) concentrated the residue distilled under reduced pressure (bp 171° C., 10 μ) to give 23.92 g

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 ml RB flask containing a solution of lauroyl chloride (19.38 g., 89 mM) in dry chloroform (200 ml) was cooled to 0° C. on an ice bath. A solution of N,N-dimethyl-1, 3-propanediamine (10.40 g., 51 mM) and triethylamine (9.40 g., 93 mM) in dry chloroform (25 ml) was added dropwise to the cold solution through an addition funnel, then allowed to warm to room temperature and stirred for 2 hours. The chloroform was removed under reduced pressure and the residue redissolved in an ethanol/water mixture (1:1) and neutralized with sodium bicarbonate, followed by extraction with chloroform (4×50 ml). The combined extracts were dried (MgSO4), concentrated, and the residue distilled under reduced pressure (bp 171° C., 10μ) to give 23.92 g. (68%) of the subject compound as an amber solid. to warm to room temperature The chloroform was removed under reduced pressure the residue redissolved in an ethanol/water mixture (1:1) followed by extraction with chloroform (4×50 ml) The combined extracts were dried (MgSO4) concentrated the residue distilled under reduced pressure (bp 171° C., 10μ) to give 23.92 g