2-(3-(环戊氧基)-4-甲氧基苯基)乙胺

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of oxamic acid (1.76 g, 20 mmol) in 1,2-dimethoxyethane (75 mL) under an argon atmosphere was added dropwise N-methylmorpholine (2.55 mL, 23 mmol) followed by ethyl chloroformate (2.20 mL, 23 mmol). After stirring for 1 h at room temperature, a solution of 2-(3-cyclopentyloxy-4-methoxy-phenyl)ethylamine (4.65 g, 20 mmol) in 1,2-dimethoxyethane (30 mL) was added over 5 min, and the resulting mixture was stirred for 2 h. Saturated aqueous ammonium chloride was added and the solvent was removed under reduced pressure. The solid residue was dissolved in methanol/methylene chloride, washed successively with water, 10% hydrochloric acid, aqueous sodium bicarbonate and water and dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 1% i-propanol/methylene chloride to provide the oxamide (1.82 g, 30%): m.p. 175°-175.5° C. the resulting mixture was stirred for 2 h the solvent was removed under reduced pressure The solid residue was dissolved in methanol/methylene chloride washed successively with water, 10% hydrochloric acid, aqueous sodium bicarbonate and water dried (potassium carbonate) The solvent was removed in vacuo the residue was purified by flash chromatography eluting with 1% i-propanol/methylene chloride

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of oxamic acid (1.76 g, 20 mmol) in 1,2-dimethoxyethane (75 mL) under an argon atmosphere was added dropwise N-methylmorpholine (2.55 mL, 23 mmol) followed by ethyl chloroformate (2.20 mL, 23 mmol). After stirring for 1 h at room temperature, a solution of 2-(3-cyclopentyloxy-4-methoxy-phenyl)ethylamine (4.65 g, 20 mmol) in 1,2-dimethoxyethane (30 mL) was added over 5 min, and the resulting mixture was stirred for 2 h. Saturated aqueous ammonium chloride was added and the solvent was removed under reduced pressure. The solid residue was dissolved in methanol/methylene chloride, washed successively with water, 10% hydrochloric acid, aqueous sodium bicarbonate and water and dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 1% i-propanol/methylene chloride to provide the oxamide (1.82 g, 30%): m.p. 175°-175.5° C. the resulting mixture was stirred for 2 h the solvent was removed under reduced pressure The solid residue was dissolved in methanol/methylene chloride washed successively with water, 10% hydrochloric acid, aqueous sodium bicarbonate and water dried (potassium carbonate) The solvent was removed in vacuo the residue was purified by flash chromatography eluting with 1% i-propanol/methylene chloride

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of lithium aluminum hydride (10.83 g, 28.5 mmol) in ether (250 mL) at 0° C. under an argon atmosphere was added dropwise a solution of 3-cyclopentyloxy-4-methoxy-β-nitrostyrene (15.00 g, 57.0 mmol) in tetrahydrofuran (85 mL). The resulting mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was cooled to 0° C. and quenched by the successive dropwise addition of water (11 mL), 15% sodium hydroxide (11 mL) and water (33 mL). The mixture was filtered through a pad of Celite™ and the filtrate was washed successively with water, 10% hydrochloric acid and water. The aqueous washes were combined, made basic with saturated aqueous potassium carbonate and extracted three times with ether and twice with methylene chloride. The organic layers were combined and dried (potassium carbonate). Removal of the solvent in vacuo provided the amine (10.80 g, 81%). A portion of the crude amine was purified by flash chromatography, eluting with 1:10:90 water/methanol/chloroform. The reaction mixture was cooled to 0° C. quenched by the successive dropwise addition of water (11 mL), 15% sodium hydroxide (11 mL) and water (33 mL) The mixture was filtered through a pad of Celite™ the filtrate was washed successively with water, 10% hydrochloric acid and water extracted three times with ether dried (potassium carbonate) Removal of the solvent in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of lithium aluminum hydride (10.83 g, 28.5 mmol) in ether (250 mL) at 0° C. under an argon atmosphere was added dropwise a solution of 3-cyclopentyloxy-4-methoxy-β-nitrostyrene (15.00 g, 57.0 mmol) in tetrahydrofuran (85 mL). The resulting mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was cooled to 0° C. and quenched by the successive dropwise addition of water (11 mL), 15% sodium hydroxide (11 mL) and water (33 mL). The mixture was filtered through a pad of Celite™ and the filtrate was washed successively with water, 10% hydrochloric acid and water. The aqueous washes were combined, made basic with saturated aqueous potassium carbonate and extracted three times with ether and twice with methylene chloride. The organic layers were combined and dried (potassium carbonate). Removal of the solvent in vacuo provided the amine (10.80 g, 81%). A portion of the crude amine was purified by flash chromatography, eluting with 1:10:90 water/methanol/chloroform. The reaction mixture was cooled to 0° C. quenched by the successive dropwise addition of water (11 mL), 15% sodium hydroxide (11 mL) and water (33 mL) The mixture was filtered through a pad of Celite™ the filtrate was washed successively with water, 10% hydrochloric acid and water extracted three times with ether dried (potassium carbonate) Removal of the solvent in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 3-cyclopentyloxy-4-methoxyphenethylamine (0.2 g, 0.85 mmol) in tetrahydrofuran (6 mL) was cooled to 0° C. and was treated with triethylamine (0.13 mL, 0.92 mmol) and methoxyacetyl chloride (0.078 mL, 0.85 mmol). The reaction was stirred under an argon atmosphere for 0.25 h, then was partitioned between methylene chloride and water. The extract was dried (potassium carbonate) and evaporated. Purification by flash chromatography, eluting with 5% methanol/chloroform, provided an oil; additional 0.1 g of impure product also obtained). was partitioned between methylene chloride and water The extract was dried (potassium carbonate) evaporated Purification by flash chromatography eluting with 5% methanol/chloroform provided an oil

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 3-cyclopentyloxy-4-methoxyphenethylamine (0.2 g, 0.85 mmol) in tetrahydrofuran (6 mL) was cooled to 0° C. and was treated with triethylamine (0.13 mL, 0.92 mmol) and methoxyacetyl chloride (0.078 mL, 0.85 mmol). The reaction was stirred under an argon atmosphere for 0.25 h, then was partitioned between methylene chloride and water. The extract was dried (potassium carbonate) and evaporated. Purification by flash chromatography, eluting with 5% methanol/chloroform, provided an oil; additional 0.1 g of impure product also obtained). was partitioned between methylene chloride and water The extract was dried (potassium carbonate) evaporated Purification by flash chromatography eluting with 5% methanol/chloroform provided an oil

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 2-(3-cyclopentyloxy-4-methoxyphenyl)ethylamine (0.47 g, 2.0 mmol) in tetrahydrofuran (10 mL) under an argon atmosphere was added trimethylsilyl isocyanate (0.42 mL, 3.1 mmol). The resulting mixture was heated at reflux for 1 h, was allowed to cool to room temperature and then was stirred overnight. The reaction mixture was again heated to reflux for an additional 5 h and allowed to cool to room temperature. Ammonium chloride was added, and the mixture was concentrated under reduced pressure. The residue was partitioned between methylene chloride and water. The organic extract was washed successively with 10%. hydrochloric acid and water and dried (potassium carbonate). Removal of the solvent in vacuo and purification of the residue by flash chromatography, eluting with 3% methanol/methylene chloride, provided the urea as a white solid: m.p. 136°-37° C. Analysis Calc. for C15H22 N2O3 : C 64.73, H 7.97, N 10.06; found: C 64.66, H 7.97, N 10.28. The resulting mixture was heated at reflux for 1 h The reaction mixture was again heated to reflux for an additional 5 h to cool to room temperature the mixture was concentrated under reduced pressure The residue was partitioned between methylene chloride and water The organic extract was washed successively with 10% hydrochloric acid and water and dried (potassium carbonate) Removal of the solvent in vacuo and purification of the residue by flash chromatography eluting with 3% methanol/methylene chloride

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of crude 2-(3-cyclopentyloxy-4-methoxyphenyl)ethylamine (0.5 g, 2.1 mmol) in pyridine (1.8 mL) under an argon atmosphere was added acetic anhydride (1.25 mL). The resulting solution was stirred at room temperature for 16 h and then concentrated under reduced pressure. The residue was dissolved in methylene chloride, washed with water and dried (sodium sulfate). The solvent was removed in vacuo, the residue was purified by flash chromatography, eluting with 4% methanol/ether, and then triturated with ether to provide the acetamide: m.p. 87°-88° C. concentrated under reduced pressure The residue was dissolved in methylene chloride washed with water dried (sodium sulfate) The solvent was removed in vacuo the residue was purified by flash chromatography eluting with 4% methanol/ether triturated with ether

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of crude 2-(3-cyclopentyloxy-4-methoxyphenyl)ethylamine (0.5 g, 2.1 mmol) in pyridine (1.8 mL) under an argon atmosphere was added acetic anhydride (1.25 mL). The resulting solution was stirred at room temperature for 16 h and then concentrated under reduced pressure. The residue was dissolved in methylene chloride, washed with water and dried (sodium sulfate). The solvent was removed in vacuo, the residue was purified by flash chromatography, eluting with 4% methanol/ether, and then triturated with ether to provide the acetamide: m.p. 87°-88° C. concentrated under reduced pressure The residue was dissolved in methylene chloride washed with water dried (sodium sulfate) The solvent was removed in vacuo the residue was purified by flash chromatography eluting with 4% methanol/ether triturated with ether

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of oxamic acid (1.76 g, 20 mmol) in 1,2-dimethoxyethane (75 mL) under an argon atmosphere was added dropwise N-methylmorpholine (2.55 mL, 23 mmol) followed by ethyl chloroformate (2.20 mL, 23 mmol). After stirring for 1 h at room temperature, a solution of 2-(3-cyclopentyloxy-4-methoxy-phenyl)ethylamine (4.65 g, 20 mmol) in 1,2-dimethoxyethane (30 mL) was added over 5 min, and the resulting mixture was stirred for 2 h. Saturated aqueous ammonium chloride was added and the solvent was removed under reduced pressure. The solid residue was dissolved in methanol/methylene chloride, washed successively with water, 10% hydrochloric acid, aqueous sodium bicarbonate and water and dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 1% i-propanol/methylene chloride to provide the oxamide (1.82 g, 30%): m.p. 175°-175.5° C. the resulting mixture was stirred for 2 h the solvent was removed under reduced pressure The solid residue was dissolved in methanol/methylene chloride washed successively with water, 10% hydrochloric acid, aqueous sodium bicarbonate and water dried (potassium carbonate) The solvent was removed in vacuo the residue was purified by flash chromatography eluting with 1% i-propanol/methylene chloride