tridecan-7-amine

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

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

Procedure: 200 mg (620 mmol) of perylene-3,4-dicarboxylic anhydride (prepared according to Example 20, below) are heated together with 250 mg (0.12 mmol) of 7-aminotridecane, 110 mg of zinc acetate dihydrate and 1.2 g of imidazole under an argon inert atmosphere at 135°-140° C. for 1 h. After cooling, the dark-red melt cake is digested with 100 ml of ethanol, and 100 ml of 15 per cent hydrochloric acid are added to the resulting suspension, and the mixture is boiled until all the ethanol has evaporated (the reaction product is readily soluble in ethanol). The solid is filtered off with suction and washed with warm water until the filtrate run-off no longer gives a yellow fluorescence. The crude product is then dried in a drying cabinet at 120° C. for 2 h and then chromatographed on silica gel using chloroform. The first coloured fraction is recrystallized by extraction with methanol. Yield 200 mg (63%) orange-red crystals showing strong solid fluorescence, m.p. 166°-168° C. Rf (chloroform/silica gel)=0.87. UV (CHCl3): λmax (ε)=506 (30250), 484 (31580). Fluorescence (CHCl3, exc. 506 nm) λmax (Irel): 540 (1), 568 (0.52). After cooling are added to the resulting suspension has evaporated (the reaction product The solid is filtered off with suction washed with warm water until the filtrate run-off no longer gives a yellow fluorescence The crude product is then dried in a drying cabinet at 120° C. for 2 h chromatographed on silica gel The first coloured fraction is recrystallized by extraction with methanol

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

Procedure: 200 mg (620 mmol) of perylene-3,4-dicarboxylic anhydride (prepared according to Example 20, below) are heated together with 250 mg (0.12 mmol) of 7-aminotridecane, 110 mg of zinc acetate dihydrate and 1.2 g of imidazole under an argon inert atmosphere at 135°-140° C. for 1 h. After cooling, the dark-red melt cake is digested with 100 ml of ethanol, and 100 ml of 15 per cent hydrochloric acid are added to the resulting suspension, and the mixture is boiled until all the ethanol has evaporated (the reaction product is readily soluble in ethanol). The solid is filtered off with suction and washed with warm water until the filtrate run-off no longer gives a yellow fluorescence. The crude product is then dried in a drying cabinet at 120° C. for 2 h and then chromatographed on silica gel using chloroform. The first coloured fraction is recrystallized by extraction with methanol. Yield 200 mg (63%) orange-red crystals showing strong solid fluorescence, m.p. 166°-168° C. Rf (chloroform/silica gel)=0.87. UV (CHCl3): λmax (ε)=506 (30250), 484 (31580). Fluorescence (CHCl3, exc. 506 nm) λmax (Irel): 540 (1), 568 (0.52). After cooling are added to the resulting suspension has evaporated (the reaction product The solid is filtered off with suction washed with warm water until the filtrate run-off no longer gives a yellow fluorescence The crude product is then dried in a drying cabinet at 120° C. for 2 h chromatographed on silica gel The first coloured fraction is recrystallized by extraction with methanol

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

Procedure: 1.2 g (3.1 mmol) of perylene-3,4,9, 10-tetracarboxylic dianhydride, 6.2 g of imidazole, 470 mg (2.36 mmol) of 7-aminotridecane (prepared according to J. Prakt. Chem. 1980, 322, 261), 150 mg (0.68 mmol) of zinc acetate dihydrate and 3.0 ml (170 mmol) of water are heated in an autoclave (100 ml) at 190° C. for 24 h. Workup is analogous to that used in the preparation of 2b. Yield 1.25 g (27%).

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

Procedure: 1.2 g (3.1 mmol) of perylene-3,4,9, 10-tetracarboxylic dianhydride, 6.2 g of imidazole, 470 mg (2.36 mmol) of 7-aminotridecane (prepared according to J. Prakt. Chem. 1980, 322, 261), 150 mg (0.68 mmol) of zinc acetate dihydrate and 3.0 ml (170 mmol) of water are heated in an autoclave (100 ml) at 190° C. for 24 h. Workup is analogous to that used in the preparation of 2b. Yield 1.25 g (27%).

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

Procedure: In a 250 mL round bottom flask, 5.00 g (25.5 mmol) dihexylketone, 19.7 g (255 mmol) ammonium acetate, and 1.10 g (17.8 mmol) sodium cyanoborohydride (NaBH3CN) were dissolved in 75 mL absolute MeOH and stirred at room temperature for 48 hours, until no significant amount of the starting material could be detected by NMR. The mixture was quenched by adding concentrated hydrochloric acid (HCl) dropwise (˜3 mL), then concentrated in vacuo. The resulting white solid was taken up in 500 mL water, basified to pH 10 with solid potassium hydroxide (KOH), and extracted with chloroform (CHCl3) twice (200 mL each). The CHCl3 fractions were combined and concentrated to give 4.12 g (81%) of 1-hexylheptylamine 1 as a pale yellow oil. 1H NMR (D2O, 500 MHz): δ 0.73 (t, 6H), 1.15-1.23 (m, 16H), 1.55 (m, 4H), 3.13 (m, 1H). The mixture was quenched by adding concentrated hydrochloric acid (HCl) dropwise (˜3 mL) concentrated in vacuo extracted with chloroform (CHCl3) twice (200 mL each) concentrated

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

Procedure: 200 mg (620 mmol) of perylene-3,4-dicarboxylic anhydride (prepared according to Example 20, below) are heated together with 250 mg (0.12 mmol) of 7-aminotridecane, 110 mg of zinc acetate dihydrate and 1.2 g of imidazole under an argon inert atmosphere at 135°-140° C. for 1 h. After cooling, the dark-red melt cake is digested with 100 ml of ethanol, and 100 ml of 15 per cent hydrochloric acid are added to the resulting suspension, and the mixture is boiled until all the ethanol has evaporated (the reaction product is readily soluble in ethanol). The solid is filtered off with suction and washed with warm water until the filtrate run-off no longer gives a yellow fluorescence. The crude product is then dried in a drying cabinet at 120° C. for 2 h and then chromatographed on silica gel using chloroform. The first coloured fraction is recrystallized by extraction with methanol. Yield 200 mg (63%) orange-red crystals showing strong solid fluorescence, m.p. 166°-168° C. Rf (chloroform/silica gel)=0.87. UV (CHCl3): λmax (ε)=506 (30250), 484 (31580). Fluorescence (CHCl3, exc. 506 nm) λmax (Irel): 540 (1), 568 (0.52). After cooling are added to the resulting suspension has evaporated (the reaction product The solid is filtered off with suction washed with warm water until the filtrate run-off no longer gives a yellow fluorescence The crude product is then dried in a drying cabinet at 120° C. for 2 h chromatographed on silica gel The first coloured fraction is recrystallized by extraction with methanol

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

Procedure: 1.2 g (3.1 mmol) of perylene-3,4,9, 10-tetracarboxylic dianhydride, 6.2 g of imidazole, 470 mg (2.36 mmol) of 7-aminotridecane (prepared according to J. Prakt. Chem. 1980, 322, 261), 150 mg (0.68 mmol) of zinc acetate dihydrate and 3.0 ml (170 mmol) of water are heated in an autoclave (100 ml) at 190° C. for 24 h. Workup is analogous to that used in the preparation of 2b. Yield 1.25 g (27%).

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

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

Procedure: In a 250 mL round bottom flask, 5.00 g (25.5 mmol) dihexylketone, 19.7 g (255 mmol) ammonium acetate, and 1.10 g (17.8 mmol) sodium cyanoborohydride (NaBH3CN) were dissolved in 75 mL absolute MeOH and stirred at room temperature for 48 hours, until no significant amount of the starting material could be detected by NMR. The mixture was quenched by adding concentrated hydrochloric acid (HCl) dropwise (˜3 mL), then concentrated in vacuo. The resulting white solid was taken up in 500 mL water, basified to pH 10 with solid potassium hydroxide (KOH), and extracted with chloroform (CHCl3) twice (200 mL each). The CHCl3 fractions were combined and concentrated to give 4.12 g (81%) of 1-hexylheptylamine 1 as a pale yellow oil. 1H NMR (D2O, 500 MHz): δ 0.73 (t, 6H), 1.15-1.23 (m, 16H), 1.55 (m, 4H), 3.13 (m, 1H). The mixture was quenched by adding concentrated hydrochloric acid (HCl) dropwise (˜3 mL) concentrated in vacuo extracted with chloroform (CHCl3) twice (200 mL each) concentrated

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

Procedure: 20.0 g (100 mmol) of 1-hexylheptylamine are heated under reflux with 20.0 g (400 mmol) of 92 percent formic acid for 1 hour. The excess formic acid is distilled off over a 10 cm Vigreux column and the reaction product which remains is subjected to fractional distillation in vacuo. Yield 18.1 g (79%)--boiling point 165° C. (1 mm Hg)-nD 20=1.4577. The reaction product contains a small content of bisformamide which can be removed by distillation only with difficulty but does not interfere in the further reactions. The excess formic acid is distilled off over a 10 cm Vigreux column the reaction product which remains is subjected to fractional distillation in vacuo can be removed by distillation only with difficulty

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

Procedure: 200 mg (620 mmol) of perylene-3,4-dicarboxylic anhydride (prepared according to Example 20, below) are heated together with 250 mg (0.12 mmol) of 7-aminotridecane, 110 mg of zinc acetate dihydrate and 1.2 g of imidazole under an argon inert atmosphere at 135°-140° C. for 1 h. After cooling, the dark-red melt cake is digested with 100 ml of ethanol, and 100 ml of 15 per cent hydrochloric acid are added to the resulting suspension, and the mixture is boiled until all the ethanol has evaporated (the reaction product is readily soluble in ethanol). The solid is filtered off with suction and washed with warm water until the filtrate run-off no longer gives a yellow fluorescence. The crude product is then dried in a drying cabinet at 120° C. for 2 h and then chromatographed on silica gel using chloroform. The first coloured fraction is recrystallized by extraction with methanol. Yield 200 mg (63%) orange-red crystals showing strong solid fluorescence, m.p. 166°-168° C. Rf (chloroform/silica gel)=0.87. UV (CHCl3): λmax (ε)=506 (30250), 484 (31580). Fluorescence (CHCl3, exc. 506 nm) λmax (Irel): 540 (1), 568 (0.52). After cooling are added to the resulting suspension has evaporated (the reaction product The solid is filtered off with suction washed with warm water until the filtrate run-off no longer gives a yellow fluorescence The crude product is then dried in a drying cabinet at 120° C. for 2 h chromatographed on silica gel The first coloured fraction is recrystallized by extraction with methanol