nonan-1-amine

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:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5 g (15.5 mmol) of perylene-3,4-dicarboxylic anhydride (prepared in accordance with Liebigs Ann. 1995, 1229–1244), 2.44 g (17 mmol) of n-nonylamine and 75 ml of N-methylpyrrolidone (NMP) was heated at 175° C. under nitrogen for 1.5 h. After cooling to room temperature, the resulting precipitate was filtered off, washed with methanol and dried under reduced pressure at 80° C. This gave 5.5 g (79%) of the desired product in the form of dark red crystals having a melting point of 201° C. After cooling to room temperature the resulting precipitate was filtered off washed with methanol dried under reduced pressure at 80° C

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

Procedure: Following example 5, heating 22.83 g (0.2 M) of 6-hexanolactone and 28.65 g (0.2 M) of 1-aminononane at 180° for 20 hours gave 11.5 g (26%) of product; b.p. 155°-165°/0.6 mm.

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

Procedure: A mixture of N-nonyl maleimide (0.01 M) prepared as described in Example 12 above, nonylamine (0.01 M), triethylamine [catalytic, 0.1 equivalent] in acetonitrile (25 ml) was stirred for 24 hours at room temperature. Acetonitrile was removed under vacuum to leave a residual liquid product which was flash chromatographed (25% ethyl acetate in petroleum ether) to yield a white solid as the desired product. prepared Acetonitrile was removed under vacuum to leave a residual liquid product which chromatographed (25% ethyl acetate in petroleum ether)

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

Procedure: A mixture of N-nonyl maleimide (0.01 M) prepared as described in Example 12 above, nonylamine (0.01 M), triethylamine [catalytic, 0.1 equivalent] in acetonitrile (25 ml) was stirred for 24 hours at room temperature. Acetonitrile was removed under vacuum to leave a residual liquid product which was flash chromatographed (25% ethyl acetate in petroleum ether) to yield a white solid as the desired product. prepared Acetonitrile was removed under vacuum to leave a residual liquid product which chromatographed (25% ethyl acetate in petroleum ether)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of itaconic anhydride (0.1 M) in pyridine (20 ml)was treated with nonylamine (0.1 M). The reaction mixture was heated to 90° C. for six hours. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. The reaction mixture was then concentrated in vacuo the residue was extracted into ethyl acetate The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid dried over sodium sulphate finally concentrated in vacuo The residue obtained was chromatographed over silica gel

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of citraconic anhydride (0.1 M) in pyridine (20 ml)was treated with nonylamine (0.1 M). The reaction mixture was heated to 90° C. for six hours. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. The reaction mixture was then concentrated in vacuo the residue was extracted into ethyl acetate The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid dried over sodium sulphate finally concentrated in vacuo The residue obtained was chromatographed over silica gel

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of citraconic anhydride (0.1 M) in pyridine (20 ml)was treated with nonylamine (0.1 M). The reaction mixture was heated to 90° C. for six hours. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. The reaction mixture was then concentrated in vacuo the residue was extracted into ethyl acetate The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid dried over sodium sulphate finally concentrated in vacuo The residue obtained was chromatographed over silica gel

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

Procedure: A solution of the carbonate (2.0 g, 3.4 mmol) produced in Example 17 in 20 mL of anhydrous dimethylformamide was added dropwise under nitrogen to a solution of nonylamine (760 μl, 4.1 mmol) and triethylamine (2.4 mL, 17 mmol) in 20 mL of anhydrous dimethylformamide at ice bath temperature. After the addition the solution was stirred at ice bath temperature for 2 hrs and at room temperature overnight. The reaction was diluted with ethyl acetate, extracted five times with water, one time with 1N HCl, five times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 1.94 g of an off-white solid. Recrystallization from diisopropyl ether gave 1.55 g (77%) of the title compound as a white crystalline solid, mp 89-91° C. After the addition the solution at room temperature overnight extracted five times with water, one time with 1N HCl, five times with saturated Na2CO3 dried (MgSO4) the solvent removed under reduced pressure

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

Procedure: A solution of the carbonate (2.0 g, 3.4 mmol) produced in Example 17 in 20 mL of anhydrous dimethylformamide was added dropwise under nitrogen to a solution of nonylamine (760 μl, 4.1 mmol) and triethylamine (2.4 mL, 17 mmol) in 20 mL of anhydrous dimethylformamide at ice bath temperature. After the addition the solution was stirred at ice bath temperature for 2 hrs and at room temperature overnight. The reaction was diluted with ethyl acetate, extracted five times with water, one time with 1N HCl, five times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 1.94 g of an off-white solid. Recrystallization from diisopropyl ether gave 1.55 g (77%) of the title compound as a white crystalline solid, mp 89-91° C. After the addition the solution at room temperature overnight extracted five times with water, one time with 1N HCl, five times with saturated Na2CO3 dried (MgSO4) the solvent removed under reduced pressure