1-(3-chloropropoxy)-4-iodobenzene

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-[(3-chloropropyl)oxy]-4-iodobenzene (10 g, 33.7 mmol) and piperidine (2.87 g, 67.4 mmol) were mixed, and stirred at 85° C. for 4 hours. After cooled to room temperature, this was concentrated, and the residue was dissolved in ethyl acetate, washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline, and the organic layer was dried with sodium sulfate. The solvent was evaporated off, and the residue was purified through silica gel column chromatography (eluate: ethyl acetate/hexane=50/50 to chloroform/methanol=10/1) to obtain the entitled compound (8.39 g, 72%) as a brown solid. After cooled to room temperature this was concentrated the residue was dissolved in ethyl acetate washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline the organic layer was dried with sodium sulfate The solvent was evaporated off the residue was purified through silica gel column chromatography (eluate: ethyl acetate/hexane=50/50 to chloroform/methanol=10/1)

反応条件: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-[(3-chloropropyl)oxy]-4-iodobenzene (10 g, 33.7 mmol) and piperidine (2.87 g, 67.4 mmol) were mixed, and stirred at 85° C. for 4 hours. After cooled to room temperature, this was concentrated, and the residue was dissolved in ethyl acetate, washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline, and the organic layer was dried with sodium sulfate. The solvent was evaporated off, and the residue was purified through silica gel column chromatography (eluate: ethyl acetate/hexane=50/50 to chloroform/methanol=10/1) to obtain the entitled compound (8.39 g, 72%) as a brown solid. After cooled to room temperature this was concentrated the residue was dissolved in ethyl acetate washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline the organic layer was dried with sodium sulfate The solvent was evaporated off the residue was purified through silica gel column chromatography (eluate: ethyl acetate/hexane=50/50 to chloroform/methanol=10/1)

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

実験手順: 4-Iodophenol (10 g, 45.4 mmol), 1-bromo-3-chloropropane (7 g, 50.0 mmol) and potassium carbonate (7.54 g, 54.5 mmol) were mixed in DMF, and stirred at room temperature for 15 hours. The reaction liquid was diluted with diethyl ether, washed with water and saturated saline in that order, and the organic layer was dried with sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified through silica gel column chromatography (eluate: ethyl acetate/hexane=5/95) to obtain the entitled compound (11.1 g, 82.3%) as a pale yellow solid. The reaction liquid washed with water and saturated saline in that order the organic layer was dried with sodium sulfate The solvent was evaporated off under reduced pressure the residue was purified through silica gel column chromatography (eluate: ethyl acetate/hexane=5/95)

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

実験手順: Following the procedure described in example 1§E, but starting from 1-(3-chloropropoxy)-4-iodobenzene (3 g), potassium carbonate (4.15 g) and piperidine (1.7 g) in N,N-dimethylformamide (30 mL) affords 3.49 g of 1-[3-(4-iodophenoxy)propyl]piperidine used without further purification.

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

実験手順: 2-methylpyrrolidine a4 (2 g, 23 mmol, 2 eq) is added into a suspension of 1-(3-chloropropoxy)-4-iodobenzene a3 (3.48 g, 11.7 mmol, 1 eq), potassium carbonate (3.24 g, 23 mmol, 2 eq) and sodium iodide (0.035 g, 0.23 mmol, 0.02 eq) in acetonitrile (120 ml), and the mixture is heated at reflux overnight. The solvent is then removed in vacuo, and the residue is dissolved in ethyl acetate. The organic layer is washed twice with a saturated solution of aqueous sodium hydrogenocarbonate, dried over magnesium sulfate, and concentrated in vacuo to give 3.65 g of a yellow oil. This oil is purified by chromatography over silicagel (dichloromethane/methanol/ammonia:98/2/0.2) to afford 2.57 g of 1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine a5 as a yellow oil. the mixture is heated at reflux overnight The solvent is then removed in vacuo the residue is dissolved in ethyl acetate The organic layer is washed twice with a saturated solution of aqueous sodium hydrogenocarbonate dried over magnesium sulfate concentrated in vacuo

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

実験手順: 2-methylpyrrolidine a4 (2 g, 23 mmol, 2 eq) is added into a suspension of 1-(3-chloropropoxy)-4-iodobenzene a3 (3.48 g, 11.7 mmol, 1 eq), potassium carbonate (3.24 g, 23 mmol, 2 eq) and sodium iodide (0.035 g, 0.23 mmol, 0.02 eq) in acetonitrile (120 ml), and the mixture is heated at reflux overnight. The solvent is then removed in vacuo, and the residue is dissolved in ethyl acetate. The organic layer is washed twice with a saturated solution of aqueous sodium hydrogenocarbonate, dried over magnesium sulfate, and concentrated in vacuo to give 3.65 g of a yellow oil. This oil is purified by chromatography over silicagel (dichloromethane/methanol/ammonia:98/2/0.2) to afford 2.57 g of 1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine a5 as a yellow oil. the mixture is heated at reflux overnight The solvent is then removed in vacuo the residue is dissolved in ethyl acetate The organic layer is washed twice with a saturated solution of aqueous sodium hydrogenocarbonate dried over magnesium sulfate concentrated in vacuo