4-(butylamino)butan-1-ol

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 8.1 g (110 mmol) of n-butylamine and 8.6 g of butyrolactone in 50 ml toluene was allowed to reflux under nitrogen atmosphere for 50 hours. Volatile solvents were removed in vacuo. To a solution of 3.18 gm (20 mmol) of the resultant N-butyl 4-hydroxybutyramide in 50 ml of toluene were added 120 ml (120 mmol) DIBAL (25% W). The solution was heated with stirring at 70° C. for 18 hours. After cooling to 0° C., the reaction was quenched with methanol (⅓ amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt. The mixture was extracted twice with EtOAc; the organic extracts were washed with brine and dried over Na2SO4. to reflux under nitrogen atmosphere for 50 hours Volatile solvents were removed in vacuo The solution was heated After cooling to 0° C. the reaction was quenched with methanol (⅓ amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt The mixture was extracted twice with EtOAc the organic extracts were washed with brine dried over Na2SO4

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 8.1 g (110 mmol) of n-butylamine and 8.6 g of butyrolactone in 50 ml toluene was allowed to reflux under nitrogen atmosphere for 50 hours. Volatile solvents were removed in vacuo. To a solution of 3.18 gm (20 mmol) of the resultant N-butyl-4-hydroxybutyramide in 50 ml of toluene were added 120 ml (120 mmol) DIBAL(25% W). The solution was heated with stirring at 70° C. for 18 hours. After cooling to 0° C., the reaction was quenched with methanol (113 amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt. The mixture was extracted twice with EtOAc; the organic extracts were washed with brine and dried over Na2SO4. to reflux under nitrogen atmosphere for 50 hours Volatile solvents were removed in vacuo The solution was heated After cooling to 0° C. the reaction was quenched with methanol (113 amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt The mixture was extracted twice with EtOAc the organic extracts were washed with brine dried over Na2SO4

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 8.1 g (110 mmol) of n-butylamine and 8.6 g of butyrolactone in 50 ml toluene was allowed to reflux under nitrogen atmosphere for 50 hours. Volatile solvents were removed in vacuo. To a solution of 3.18 gm (20 mmol) of the resultant N-butyl-4-hydroxybutyramide in 50 ml of toluene were added 120 ml (120 mmol) DIBAL(25% W). The solution was heated with stirring at 70° C. for 18 hours. After cooling to 0° C., the reaction was quenched with methanol (113 amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt. The mixture was extracted twice with EtOAc; the organic extracts were washed with brine and dried over Na2SO4. to reflux under nitrogen atmosphere for 50 hours Volatile solvents were removed in vacuo The solution was heated After cooling to 0° C. the reaction was quenched with methanol (113 amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt The mixture was extracted twice with EtOAc the organic extracts were washed with brine dried over Na2SO4

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a three neck flask fitted with a mechanical stirrer, a thermometer, and a condenser, is added 124 g (1 mole) of 4-fluorobenzaldehyde, 145.3 g (1 mole) of N-butyl-N-4-hydroxybutylamine, 138.2 g (1 mole) of anhydrous potassium carbonate, and dimethylsulfoxide. The mixture is then heated at 95° C. until the reaction is complete. After cooling to room temperature, the solution is poured into a four-fold excess of ice water, and the solid product is collected by filtration and purified by recrystallization from tetrahydrofuran/benzene. To a three neck flask fitted with a mechanical stirrer After cooling to room temperature the solid product is collected by filtration purified by recrystallization from tetrahydrofuran/benzene

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a three neck flask fitted with a mechanical stirrer, a thermometer, and a condenser, is added 124 g (1 mole) of 4-fluorobenzaldehyde, 145.3 g (1 mole) of N-butyl-N-4-hydroxybutylamine, 138.2 g (1 mole) of anhydrous potassium carbonate, and dimethylsulfoxide. The mixture is then heated at 95° C. until the reaction is complete. After cooling to room temperature, the solution is poured into a four-fold excess of ice water, and the solid product is collected by filtration and purified by recrystallization from tetrahydrofuran/benzene. To a three neck flask fitted with a mechanical stirrer After cooling to room temperature the solid product is collected by filtration purified by recrystallization from tetrahydrofuran/benzene

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

Procedure: 21.1 Parts of 3-phenyl-7-[(6-chloro-4-diethylamino-s-triazine-2-yl)amino]coumarin and 14.2 parts of N-butylamino-4-butanol were added to 20 parts of tetrahydrofuran and reacted for 6 hours under reflux. The reaction product was poured into water, and the crystals thus precipitated were collected by filtration. The product was recrystallized from a mixed solvent of chloroform:ethyl acetate (1:1 by volume) to obtain 20 parts of 3-phenyl-7-[[6-(4-hydroxybutylbutylamino)-4-diethylamino-s-triazine-2-yl]amino]coumarin. The resulting compound had a melting point of from 124° to 126° C. reacted for 6 hours under reflux the crystals thus precipitated were collected by filtration The product was recrystallized from a mixed solvent of chloroform:ethyl acetate (1:1 by volume)

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

Procedure: In 75 ml of dioxane were dissolved 5.19 g (19.7 mmol) of 3-benzyloxybromobenzene and 3.72 g (25.6 mmol) of 4-butylamino-1-butanol. To this mixture was added 5.89 g (29.5 mmol) of potassium hexamethyldisilazide and the mixture was stirred with heating at 100° C. for 22 hours. After the reaction mixture was poured into 200 ml of water, extraction with chloroform, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give 2.22 g of a light brown oily matter (yield: 34.4%). washing with a saturated saline solution drying over anhydrous sodium sulfate, and concentration The residue was purified by silica gel column chromatography to give 2.22 g of a light brown oily matter (yield: 34.4%)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 8.1 g (110 mmol) of n-butylamine and 8.6 g of butyrolactone in 50 ml toluene was allowed to reflux under nitrogen atmosphere for 50 hours. Volatile solvents were removed in vacuo. To a solution of 3.18 gm (20 mmol) of the resultant N-butyl-4-hydroxybutyramide in 50 ml of toluene were added 120 ml (120 mmol) DIBAL(25% W). The solution was heated with stirring at 70° C. for 18 hours. After cooling to 0° C., the reaction was quenched with methanol (1/3 amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt. The mixture was extracted twice with EtOAc; the organic extracts were washed with brine and dried over Na2SO4. to reflux under nitrogen atmosphere for 50 hours Volatile solvents were removed in vacuo The solution was heated After cooling to 0° C. the reaction was quenched with methanol (1/3 amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt The mixture was extracted twice with EtOAc the organic extracts were washed with brine dried over Na2SO4

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

Procedure: A solution of 8.1 g (110 mmol) of n-butylamine and 8.6 g of butyrolactone in 50 ml toluene was allowed to reflux under nitrogen atmosphere for 50 hours. Volatile solvents were removed in vocuo. To a solution of 3.18 gm (20 mmol) of the resultant N-butyl-4-hydroxybutyramide in 50 ml of toluene were added 120 ml (120 mmol) DIBAL (25% W). The solution was heated with stirring at 70.C for 18 hours. After cooling to 0.C, the reaction was quenched with methanol (⅓ amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt. The mixture was extracted twice with EtOAc; the organic extracts were washed with brine and dried over Na2SO4. to reflux under nitrogen atmosphere for 50 hours Volatile solvents were removed in vocuo The solution was heated the reaction was quenched with methanol (⅓ amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt The mixture was extracted twice with EtOAc the organic extracts were washed with brine dried over Na2SO4

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 8.1 g (110 mmol) of n-butylamine and 8.6 g of butyrolactone in 50 ml toluene was allowed to reflux under nitrogen atmosphere for 50 hours. Volatile solvents were removed in vacuo. To a solution of 3.18 gm (20 mmol) of the resultant N-butyl 4-hydroxybutyramide in 50 ml of toluene were added 120 ml (120 mmol) DIBAL (25% W). The solution was heated with stirring at 70° C. for 18 hours. After cooling to 0° C., the reaction was quenched with methanol (⅓ amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt. The mixture was extracted twice with EtOAc; the organic extracts were washed with brine and dried over Na2SO4. to reflux under nitrogen atmosphere for 50 hours Volatile solvents were removed in vacuo The solution was heated After cooling to 0° C. the reaction was quenched with methanol (⅓ amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt The mixture was extracted twice with EtOAc the organic extracts were washed with brine dried over Na2SO4

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 8.1 g (110 mmol) of n-butylamine and 8.6 g of butyrolactone in 50 ml toluene was allowed to reflux under nitrogen atmosphere for 50 hours. Volatile solvents were removed in vacuo. To a solution of 3.18 gm (20 mmol) of the resultant N-butyl-4-hydroxybutyramide in 50 ml of toluene were added 120 ml (120 mmol) DIBAL(25% W). The solution was heated with stirring at 70° C. for 18 hours. After cooling to 0° C., the reaction was quenched with methanol (113 amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt. The mixture was extracted twice with EtOAc; the organic extracts were washed with brine and dried over Na2SO4. to reflux under nitrogen atmosphere for 50 hours Volatile solvents were removed in vacuo The solution was heated After cooling to 0° C. the reaction was quenched with methanol (113 amount of DIBAL solution was used) followed by addition of saturated solution of Rochelle's salt The mixture was extracted twice with EtOAc the organic extracts were washed with brine dried over Na2SO4

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a three neck flask fitted with a mechanical stirrer, a thermometer, and a condenser, is added 124 g (1 mole) of 4-fluorobenzaldehyde, 145.3 g (1 mole) of N-butyl-N-4-hydroxybutylamine, 138.2 g (1 mole) of anhydrous potassium carbonate, and dimethylsulfoxide. The mixture is then heated at 95° C. until the reaction is complete. After cooling to room temperature, the solution is poured into a four-fold excess of ice water, and the solid product is collected by filtration and purified by recrystallization from tetrahydrofuran/benzene. To a three neck flask fitted with a mechanical stirrer After cooling to room temperature the solid product is collected by filtration purified by recrystallization from tetrahydrofuran/benzene