N-(2-aminoethyl)morpholine-4-carboxamide

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-(2-((2-hydroxy-3-(4-(2-(2-methylpropoxy)ethoxy)phenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide was prepared in accordance with example 4 using 10.1 g of the neutral sulphate of N-2-aminoethyl-4-morpholinecarboxamide and 9.3 g of 3-(4-(2-(2-methylpropoxy)ethoxy)phenoxy-1,2-epoxypropane as starting materials. Yield 3.9 g. Melting point 95°-96° C. (base). The structure was determined using NMR-analysis.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 12.0 g of the neutral sulphate of N-2-aminoethyl-4-morpholinecarboxamide and 2.16 g NaOH was refluxed in 100 ml of ethanol for 1 h. Thereafter 10 g of 3-(4-(2-cyclobutylmethoxyethoxy)phenoxy-1,2-epoxypropane in 50 ml of ethanol was added and the mixture refluxed for 20 h, filtered, and evaporated. The residue was dissolved in 175 ml of ethyl acetate and washed twice with water. Thereafter the title compound crystallized from the ethyl acetate phase. The crystals were filtered off and washed with ether. Yield 7.1 g. Melting point 91°-93° C. (base). The structure was determined using NMR-analysis. the mixture refluxed for 20 h filtered evaporated The residue was dissolved in 175 ml of ethyl acetate washed twice with water Thereafter the title compound crystallized from the ethyl acetate phase The crystals were filtered off washed with ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 12.0 g of the neutral sulphate of N-2-aminoethyl-4-morpholinecarboxamide and 2.16 g NaOH was refluxed in 100 ml of ethanol for 1 h. Thereafter 10 g of 3-(4-(2-cyclobutylmethoxyethoxy)phenoxy-1,2-epoxypropane in 50 ml of ethanol was added and the mixture refluxed for 20 h, filtered, and evaporated. The residue was dissolved in 175 ml of ethyl acetate and washed twice with water. Thereafter the title compound crystallized from the ethyl acetate phase. The crystals were filtered off and washed with ether. Yield 7.1 g. Melting point 91°-93° C. (base). The structure was determined using NMR-analysis. the mixture refluxed for 20 h filtered evaporated The residue was dissolved in 175 ml of ethyl acetate washed twice with water Thereafter the title compound crystallized from the ethyl acetate phase The crystals were filtered off washed with ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 26.2 g of the hydrochloride of N-2-aminoethyl-4-morpholinecarboxamide and 5.0 g of NaOH were refluxed in 175 ml of ethanol for 1 h. Thereafter 22 g of 3-(4-(2-cyclopropylmethoxyethoxy)phenoxy)-1,2-epoxypropane in 100 ml of ethanol was added and the resulting mixture refluxed for 16 h, filtered, and evaporated. The residue was dissolved in 300 ml of ethyl acetate and washed three times with water. The organic phase was then extracted with 250 ml of water at pH 5 (HCl). The aqueous phase was then made alkaline and extracted with methylene chloride. The methylene chloride phase was dried over Na2SO4, filtered, and evaporated. The residue was treated with ether and recrystallized from ethyl acetate. Yield 8.0 g. Melting point 80°-81° C. (base). The structure was determined using NMR-analysis. the resulting mixture refluxed for 16 h filtered evaporated The residue was dissolved in 300 ml of ethyl acetate washed three times with water The organic phase was then extracted with 250 ml of water at pH 5 (HCl) extracted with methylene chloride The methylene chloride phase was dried over Na2SO4 filtered evaporated The residue was treated with ether recrystallized from ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 12.0 g of the neutral sulphate of N-2-aminoethyl-4-morpholinecarboxamide, 2.16 g NaOH and 100 ml of absolute ethanol were refluxed 1 h. During continuing reflux 8.6 g of 3-(4-(2-ethoxyethoxy)phenoxy-1,2-epoxypropane in 50 ml of abs. ethanol was added little by little. The resulting mixture was refluxed over night, filtered and evaporated. The residue was dissolved in 200 ml of ethyl acetate and extracted twice with water. The water phase was treated with NaCl and extracted twice with ethyl acetate. The ethyl acetate phase was dried, filtered and evaporated. The residue was crystallized from ether, and recrystallized from ethyl acetate. Yield 1.1 g. Melting point 75°-77° C. (base). The structure was determined using NMR analysis. The resulting mixture was refluxed over night filtered evaporated The residue was dissolved in 200 ml of ethyl acetate extracted twice with water The water phase was treated with NaCl extracted twice with ethyl acetate The ethyl acetate phase was dried filtered evaporated The residue was crystallized from ether recrystallized from ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 12.0 g of the neutral sulphate of N-2-aminoethyl-4-morpholinecarboxamide, 2.16 g NaOH and 100 ml of absolute ethanol were refluxed 1 h. During continuing reflux 8.6 g of 3-(4-(2-ethoxyethoxy)phenoxy-1,2-epoxypropane in 50 ml of abs. ethanol was added little by little. The resulting mixture was refluxed over night, filtered and evaporated. The residue was dissolved in 200 ml of ethyl acetate and extracted twice with water. The water phase was treated with NaCl and extracted twice with ethyl acetate. The ethyl acetate phase was dried, filtered and evaporated. The residue was crystallized from ether, and recrystallized from ethyl acetate. Yield 1.1 g. Melting point 75°-77° C. (base). The structure was determined using NMR analysis. The resulting mixture was refluxed over night filtered evaporated The residue was dissolved in 200 ml of ethyl acetate extracted twice with water The water phase was treated with NaCl extracted twice with ethyl acetate The ethyl acetate phase was dried filtered evaporated The residue was crystallized from ether recrystallized from ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4 g of 3-(4-(2-methoxyethoxy)phenoxy)-1,2-epoxypropane, 5.8 g of the sulphate of N-2-aminoethyl-4-morpholinecarboxamide, and 5.8 g of K2CO3 were refluxed in 2-propanol for 2 days. The mixture was filtered and concentrated in vacuo. The residue was dissolved in methylene chloride and washed with H2O. The organic phase was dried over Na2SO4, filtered and evaporated. The product was recrystallized from ethyl acetate. Yield 2.3 g. Melting point 69° C. (base). The structure was determined using NMR and equivalent weight. The mixture was filtered concentrated in vacuo The residue was dissolved in methylene chloride washed with H2O The organic phase was dried over Na2SO4 filtered evaporated The product was recrystallized from ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-(2-((2-hydroxy-3-(4-(2-(2-methylpropoxy)ethoxy)phenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide was prepared in accordance with example 4 using 10.1 g of the neutral sulphate of N-2-aminoethyl-4-morpholinecarboxamide and 9.3 g of 3-(4-(2-(2-methylpropoxy)ethoxy)phenoxy-1,2-epoxypropane as starting materials. Yield 3.9 g. Melting point 95°-96° C. (base). The structure was determined using NMR-analysis.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 12.0 g of the neutral sulphate of N-2-aminoethyl-4-morpholinecarboxamide and 2.16 g NaOH was refluxed in 100 ml of ethanol for 1 h. Thereafter 10 g of 3-(4-(2-cyclobutylmethoxyethoxy)phenoxy-1,2-epoxypropane in 50 ml of ethanol was added and the mixture refluxed for 20 h, filtered, and evaporated. The residue was dissolved in 175 ml of ethyl acetate and washed twice with water. Thereafter the title compound crystallized from the ethyl acetate phase. The crystals were filtered off and washed with ether. Yield 7.1 g. Melting point 91°-93° C. (base). The structure was determined using NMR-analysis. the mixture refluxed for 20 h filtered evaporated The residue was dissolved in 175 ml of ethyl acetate washed twice with water Thereafter the title compound crystallized from the ethyl acetate phase The crystals were filtered off washed with ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 26.2 g of the hydrochloride of N-2-aminoethyl-4-morpholinecarboxamide and 5.0 g of NaOH were refluxed in 175 ml of ethanol for 1 h. Thereafter 22 g of 3-(4-(2-cyclopropylmethoxyethoxy)phenoxy)-1,2-epoxypropane in 100 ml of ethanol was added and the resulting mixture refluxed for 16 h, filtered, and evaporated. The residue was dissolved in 300 ml of ethyl acetate and washed three times with water. The organic phase was then extracted with 250 ml of water at pH 5 (HCl). The aqueous phase was then made alkaline and extracted with methylene chloride. The methylene chloride phase was dried over Na2SO4, filtered, and evaporated. The residue was treated with ether and recrystallized from ethyl acetate. Yield 8.0 g. Melting point 80°-81° C. (base). The structure was determined using NMR-analysis. the resulting mixture refluxed for 16 h filtered evaporated The residue was dissolved in 300 ml of ethyl acetate washed three times with water The organic phase was then extracted with 250 ml of water at pH 5 (HCl) extracted with methylene chloride The methylene chloride phase was dried over Na2SO4 filtered evaporated The residue was treated with ether recrystallized from ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 12.0 g of the neutral sulphate of N-2-aminoethyl-4-morpholinecarboxamide, 2.16 g NaOH and 100 ml of absolute ethanol were refluxed 1 h. During continuing reflux 8.6 g of 3-(4-(2-ethoxyethoxy)phenoxy-1,2-epoxypropane in 50 ml of abs. ethanol was added little by little. The resulting mixture was refluxed over night, filtered and evaporated. The residue was dissolved in 200 ml of ethyl acetate and extracted twice with water. The water phase was treated with NaCl and extracted twice with ethyl acetate. The ethyl acetate phase was dried, filtered and evaporated. The residue was crystallized from ether, and recrystallized from ethyl acetate. Yield 1.1 g. Melting point 75°-77° C. (base). The structure was determined using NMR analysis. The resulting mixture was refluxed over night filtered evaporated The residue was dissolved in 200 ml of ethyl acetate extracted twice with water The water phase was treated with NaCl extracted twice with ethyl acetate The ethyl acetate phase was dried filtered evaporated The residue was crystallized from ether recrystallized from ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4 g of 3-(4-(2-methoxyethoxy)phenoxy)-1,2-epoxypropane, 5.8 g of the sulphate of N-2-aminoethyl-4-morpholinecarboxamide, and 5.8 g of K2CO3 were refluxed in 2-propanol for 2 days. The mixture was filtered and concentrated in vacuo. The residue was dissolved in methylene chloride and washed with H2O. The organic phase was dried over Na2SO4, filtered and evaporated. The product was recrystallized from ethyl acetate. Yield 2.3 g. Melting point 69° C. (base). The structure was determined using NMR and equivalent weight. The mixture was filtered concentrated in vacuo The residue was dissolved in methylene chloride washed with H2O The organic phase was dried over Na2SO4 filtered evaporated The product was recrystallized from ethyl acetate