ethyl dodecanoate

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

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

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 23 g of ethyl dodecanoate and 62.7 g of ethylenediamine in 100 ml of tetrahydrofuran (THF) was refluxed for 3 hours and the excess THF was distilled off. The reaction mixture was heated at 100° C. for 16 hours, cooled to room temperature, poured into cold water and extracted with ether. After drying, the organic solution was concentrated to give 15.7 g of crude product and this was recrystallized from ether-hexane to give 10.9 g of pure product, m.p. 64°-66° C. the excess THF was distilled off cooled to room temperature poured into cold water extracted with ether After drying the organic solution was concentrated to give 15.7 g of crude product this was recrystallized from ether-hexane

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

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

Procedure: 13.7 g (92.6 mmoles) N-[2-(2-Hydroxyethoxy)ethyl]ethylenediamine and 19.6 g (86 mmoles) of ethyl dodecanoate were mixed and heated in a flask equipped with a Dean-Stark trap. After the separated ethanol and water were distilled off, the residue was kugelrohr distilled at 160°-170° C./0.1 mm to give 13.6 g (50.7%) of crude product. Recrystallization from ethyl acetate/hexane gave white crystalline material, m.p. 58°-60° C. heated in a flask equipped with a Dean-Stark trap After the separated ethanol and water were distilled off the residue was kugelrohr distilled at 160°-170° C./0.1 mm

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

Procedure: 13.7 g (92.6 mmoles) N-[2-(2-Hydroxyethoxy)ethyl]ethylenediamine and 19.6 g (86 mmoles) of ethyl dodecanoate were mixed and heated in a flask equipped with a Dean-Stark trap. After the separated ethanol and water were distilled off, the residue was kugelrohr distilled at 160°-170° C./0.1 mm to give 13.6 g (50.7%) of crude product. Recrystallization from ethyl acetate/hexane gave white crystalline material, m.p. 58°-60° C. heated in a flask equipped with a Dean-Stark trap After the separated ethanol and water were distilled off the residue was kugelrohr distilled at 160°-170° C./0.1 mm

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

Procedure: 22.84 g. (100 mmoles) of ethyl dodecanoate and 15.34 g. (118 mmoles) of N1 -isopropyl-2-methyl-1,2-propanediamine was heated at 130°-230° C. until approximately 100 mmoles of ethanol was collected. Toluene was then cautiously added and the heating was continued until no more water separated. The solution was acidified, the aqueous layer was separated and basified with NaOH. This was extracted with ethyl acetate, the organic extract was dried and concentrated. The oil was distilled at 150°-152° C./1.2 mm to give 16.74 g (58%) of product. was collected Toluene was then cautiously added separated the aqueous layer was separated This was extracted with ethyl acetate the organic extract was dried concentrated The oil was distilled at 150°-152° C./1.2 mm

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

Procedure: 22.84 g. (100 mmoles) of ethyl dodecanoate and 15.34 g. (118 mmoles) of N1 -isopropyl-2-methyl-1,2-propanediamine was heated at 130°-230° C. until approximately 100 mmoles of ethanol was collected. Toluene was then cautiously added and the heating was continued until no more water separated. The solution was acidified, the aqueous layer was separated and basified with NaOH. This was extracted with ethyl acetate, the organic extract was dried and concentrated. The oil was distilled at 150°-152° C./1.2 mm to give 16.74 g (58%) of product. was collected Toluene was then cautiously added separated the aqueous layer was separated This was extracted with ethyl acetate the organic extract was dried concentrated The oil was distilled at 150°-152° C./1.2 mm

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

Procedure: 1-(2-methoxyethyl)-2-undecyl-2-imidazoline was similarly prepared from 30.8 g of ethyl dodecanoate and 16 g of N-(2-methoxyethyl)ethylenediamine. Distillation of the crude product at 150° C./0.1 mm gave 9.3 g of pure product. Distillation of the crude product at 150° C./0.1 mm

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

Procedure: 1-(2-methoxyethyl)-2-undecyl-2-imidazoline was similarly prepared from 30.8 g of ethyl dodecanoate and 16 g of N-(2-methoxyethyl)ethylenediamine. Distillation of the crude product at 150° C./0.1 mm gave 9.3 g of pure product. Distillation of the crude product at 150° C./0.1 mm

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

Procedure: 8 g (60.6 mmoles) of 4-(2-aminoethylamino)butanol and 12.5 g of ethyl dodecanoate were treated as under Example 25. The resulting 10.8 g of an oil (66.7%) was dissolved in 100 ml of hexane and kept in the freezer to give 8.8 g of pure product, m.p. 58°-60° C.