1,9-dibromononane

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dimethylformamide (150 ml) was added to 21.3 g of 1,9-dibromononane, 19.8 g of 4-hydroxybenzaldehyde and 21.7 g of potassium carbonate, and the mixture was stirred at 90° C. for 1.5 hours. The reaction mixture was cooled to room temperature and poured into water, and the thus formed precipitate was washed with water and then dried under a reduced pressure to obtain 26.9 g of 1,9-bis(4-formylphenoxy)nonane. The reaction mixture was cooled to room temperature the thus formed precipitate was washed with water dried under a reduced pressure

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dimethylformamide (150 ml) was added to 21.3 g of 1,9-dibromononane, 19.8 g of 4-hydroxybenzaldehyde and 21.7 g of potassium carbonate, and the mixture was stirred at 90° C. for 1.5 hours. The reaction mixture was cooled to room temperature and poured into water, and the thus formed precipitate was washed with water and then dried under a reduced pressure to obtain 26.9 g of 1,9-bis(4-formylphenoxy)nonane. The reaction mixture was cooled to room temperature the thus formed precipitate was washed with water dried under a reduced pressure

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,9-Dibromononane (mmol) was added to a solution (30 mL) of isoquinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting purple solid was isolated in a 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 10.17 (1H, d, C1-H), 8.85 (1H, d, C3-H), 8.62 (1H, d, C8-H), 8.49 (1H, d, C4-H), 8.36 (2H, d, C7-H), 8.26 (2H, t, C5-H), 8.08 (1H, t, C6-H), 4.72 (2H, t, C′1-CH2), 2.02 (2H, m, C′2-CH2), 1.78 (1H, m, C′3-CH2), 1.19-1.50 (4H, m, C′3-5-CH2). The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting purple solid was isolated in a 92% yield

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,9-Dibromononane (mmol) was added to a solution (30 mL) of dry quinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting purple solid was isolated in a 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.68 (1H, d, C2-H), 9.34 (1H, d, C3-H), 8.67 (1H, d, C8-H), 8.55 (1H, d, C4-H), 8.27 (2H, m, C5&C7-H), 8.07 (1H, d, C6-H), 5.09 (2H, t, C′1-CH2), 1.95 (2H, m, C′2-CH2), 1.19-1.45 (5H, m, C′3-5-CH2). The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting purple solid was isolated in a 92% yield

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,9-Dibromononane (mmol) was added to a solution (30 mL) of dry pyridine, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting clear liquid was isolated in a 87% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.17 (2H, d, C2&C6-H), 8.61 (1H, t, C4-H), 8.18 (2H, t, C3&C5-H), 4.63 (2H, t, C′1-CH2), 1.89 (2H, m, C′2-CH2), 1.22 (5H, m, C′3-5-CH2); 13C NMR (75 MHz, DMSO-D6) δ 145.3, 144.5, 127.9, 60.5, 30.7, 28.4, 28.2, 25.3. The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting clear liquid was isolated in a 87% yield

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,9-Dibromononane (mmol) was added to a solution (30 mL) of dry pyridine, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting clear liquid was isolated in a 87% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.17 (2H, d, C2&C6-H), 8.61 (1H, t, C4-H), 8.18 (2H, t, C3&C5-H), 4.63 (2H, t, C′1-CH2), 1.89 (2H, m, C′2-CH2), 1.22 (5H, m, C′3-5-CH2); 13C NMR (75 MHz, DMSO-D6) δ 145.3, 144.5, 127.9, 60.5, 30.7, 28.4, 28.2, 25.3. The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting clear liquid was isolated in a 87% yield

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Trans-4-(methylamino)cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 5, 0.5 g, 0.001 mol), 1,9-dibromononane (2.9 mL, 0.01 mol) and triethylamine (0.44 mL, 0.003 mol) were mixed together under nitrogen atmosphere and stirred at 70° C. for 94 hours. The reaction mixture was evaporated and purified by column chromatography with silica gel, eluting with chloroform/methanol (from 100 to 4:1) to give the title compound as a brown oil (55%). The reaction mixture was evaporated purified by column chromatography with silica gel eluting with chloroform/methanol (from 100 to 4:1)

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dimethylformamide (150 ml) was added to 21.3 g of 1,9-dibromononane, 19.8 g of 4-hydroxybenzaldehyde and 21.7 g of potassium carbonate, and the mixture was stirred at 90° C. for 1.5 hours. The reaction mixture was cooled to room temperature and poured into water, and the thus formed precipitate was washed with water and then dried under a reduced pressure to obtain 26.9 g of 1,9-bis(4-formylphenoxy)nonane. The reaction mixture was cooled to room temperature the thus formed precipitate was washed with water dried under a reduced pressure

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 28.61 Grams of 1,9-dibromononane and 52.46 g of triphenylphosphine were weighed out and placed in a 500-mL three-necked flask. These compounds were dissolved in 100 mL of N-methylpyrrolidone. This solution was stirred at 80° C. for 5 hours and the resultant reaction mixture was cooled to room temperature. Thereafter, the reaction mixture was poured into 500 mL of ethyl acetate kept being sufficiently stirred. The solid precipitated was collected by suction filtration and washed with 50 mL of ethyl acetate twice. The solid obtained was placed on a Petri dish and dried at room temperature under vacuum until the mass of the solid became constant. As a result, nonamethylenebis(triphenylphosphonium)dibromide was obtained as a white solid in an amount of 73 g (yield: 90%). placed in a 500-mL three-necked flask the resultant reaction mixture was cooled to room temperature kept being sufficiently stirred The solid precipitated was collected by suction filtration washed with 50 mL of ethyl acetate twice The solid obtained dried at room temperature under vacuum until the mass of the solid

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 103 g (0.36 mol) 1,9-dibromononane is stirred at 120° C. and a solution of 11.8 g (0.045 mol) triphenylphosphine in 120 ml toluene is added within 8 hours. After a further 10 hours at 120° C. it is allowed to cool, the supernatant is decanted and the viscous residue is stirred twice with isohexane at 60° C. After drying on a rotary evaporator in a stream of nitrogen 22.4 g (91%) 65 was obtained as a nearly colourless resin. to cool the supernatant is decanted After drying on a rotary evaporator in a stream of nitrogen 22.4 g (91%) 65 was obtained as a nearly colourless resin

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

実験手順: The compound was prepared by a method similar to Example 2 from 6-hydroxyflavone, 1,9-dibromononane and 4-methyl piperazine: mp 77°-80° C.

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

実験手順: The compound was prepared by a method similar to Example 2 from 6-hydroxyflavone, 1,9-dibromononane and dimethylamine: mp 52°-53° C.