heptadecan-1-amine

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

Procedure: C17BocSar1 : the product C17BocSar1 is obtained by coupling heptadecylamine with BocSar1 in the presence of dicyclohexylcarbodiimide (DCCI). 3.78 g (0.02 mole) of BocSar and 2.06 g (0.01 mole) of DCCI are mixed cold (at 0° C.) in 100 ml of chloroform. A copious precipitate of dicyclohexylurea (DCU) is formed. The mixture is left for 30 minutes at 0° C., with agitation, and 2.55 g (0.01 mole) of heptadecylamine are added. The reaction is left to proceed for 20 hours. The precipitate is filtered off and washed, the filtrate is recovered, the chloroform is evaporated off, the residue is taken up in 50 ml of THF, the mixture is cooled to 0° C. and filtered to remove the maximum amount of dicyclohexylurea, and the precipitate is washed with the minimum amount of cold THF. C17BocSar1 : the product C17BocSar1 is obtained

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3,3-dibromo-2,2′-bithiophene (4.92 g, 15.3 mmol), t-BuONa (3.54 g, 36.8 mmol), Pd2 dba3 (0.35 g, 0.382 mmol) and BINAP (0.95 g, 1.53 mmol) in toluene (38 mL) under an argon atmosphere was added 9-octylnonylamine (4 g, 15.7 mmol). The reaction mixture was subsequently stirred at 110° C. over a period of 7 hours. The reaction mixture was allowed to cool to room temperature followed by the addition of water. The organic layer was removed and the remaining aqueous phase extracted several times with diethyl ether. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. Purification by column chromatography using hexanes as the eluant afforded the title compound as a light green solid (5.2 g, 81% yield): mp: 60° C.; GC-Ms: 417.5; 1H NMR (400 MHz, CDCl3, ppm) δ: 7.11(d, 2H), 7.02-7.01(d, 2H), 4.23-4.19(m, 1H), 2.08(m, 2H), 1.85-1.80(m, 2H), 1.22-1.07(m, 24 H), 0.86-0.82(t, 6 H); 13C NMR (100 MHz, CDCl3, ppm) δ: 144.2, 122, 4, 114.9, 59.9, 35.4, 31.9, 29.4, 29.3, 26.7, 22.8, 14.2. to cool to room temperature The organic layer was removed the remaining aqueous phase extracted several times with diethyl ether The combined organic layers were dried over anhydrous magnesium sulfate concentrated Purification by column chromatography

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

Procedure: C17BocSar1 : the product C17BocSar1 is obtained by coupling heptadecylamine with BocSar1 in the presence of dicyclohexylcarbodiimide (DCCI). 3.78 g (0.02 mole) of BocSar and 2.06 g (0.01 mole) of DCCI are mixed cold (at 0° C.) in 100 ml of chloroform. A copious precipitate of dicyclohexylurea (DCU) is formed. The mixture is left for 30 minutes at 0° C., with agitation, and 2.55 g (0.01 mole) of heptadecylamine are added. The reaction is left to proceed for 20 hours. The precipitate is filtered off and washed, the filtrate is recovered, the chloroform is evaporated off, the residue is taken up in 50 ml of THF, the mixture is cooled to 0° C. and filtered to remove the maximum amount of dicyclohexylurea, and the precipitate is washed with the minimum amount of cold THF. C17BocSar1 : the product C17BocSar1 is obtained