N-丙基-2,3-二氢-1H-茚-2-胺

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

实验步骤: In 100 ml of tetrahydrofuran was suspended 5.7 g of lithium aluminum hydride, and 150 ml of a solution containing 18.9 g of 2-(propionylamino) indane dissolved in tetrahydrofuran was added dropwise to the suspension. The mixture was refluxed under heating for 2 hours. After cooling, excess lithium aluminum hydride was treated with a saturated ammonium chloride aqueous solution, and insolubles were removed by filtration. The filtrate was concentrated, and chloroform was added to the residue. The mixture was washed with water and dried, and the solvent was removed to obtain 17.5 g of 2-(propylamino) indane. was added dropwise to the suspension The mixture was refluxed under heating for 2 hours After cooling were removed by filtration The filtrate was concentrated chloroform was added to the residue The mixture was washed with water dried the solvent was removed

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

实验步骤: In 100 ml of tetrahydrofuran was suspended 5.7 g of lithium aluminum hydride, and 150 ml of a solution containing 18.9 g of 2-(propionylamino) indane dissolved in tetrahydrofuran was added dropwise to the suspension. The mixture was refluxed under heating for 2 hours. After cooling, excess lithium aluminum hydride was treated with a saturated ammonium chloride aqueous solution, and insolubles were removed by filtration. The filtrate was concentrated, and chloroform was added to the residue. The mixture was washed with water and dried, and the solvent was removed to obtain 17.5 g of 2-(propylamino) indane. was added dropwise to the suspension The mixture was refluxed under heating for 2 hours After cooling were removed by filtration The filtrate was concentrated chloroform was added to the residue The mixture was washed with water dried the solvent was removed

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

实验步骤: To a solution of N-indan-2-yl-propylamine (9.5 g, 54.3 mmol) in methylene chloride was added aq. Na2CO3 (150 mL, 3%) followed by propionyl chloride (7.5 mL, 86.3 mmol). The mixture was stirred at ambient temperature for 1 h. The layers were separated and the organic layer was washed with water, separated and dried (MgSO4). Evaporation of the solvent yielded 7 g (56%) of N-indan-2-yl-N-propyl-propionamide. MS m/e 231 (1, M+), 116 (100), 117 (23), 57 (11), 146 (9). The layers were separated the organic layer was washed with water separated dried (MgSO4) Evaporation of the solvent

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

实验步骤: To a solution of N-indan-2-yl-propylamine (9.5 g, 54.3 mmol) in methylene chloride was added aq. Na2CO3 (150 mL, 3%) followed by propionyl chloride (7.5 mL, 86.3 mmol). The mixture was stirred at ambient temperature for 1 h. The layers were separated and the organic layer was washed with water, separated and dried (MgSO4). Evaporation of the solvent yielded 7 g (56%) of N-indan-2-yl-N-propyl-propionamide. MS m/e 231 (1, M+), 116 (100), 117 (23), 57 (11), 146 (9). The layers were separated the organic layer was washed with water separated dried (MgSO4) Evaporation of the solvent

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

实验步骤: To a stirred solution of Indan-2-yl-propyl-amine (20.0 g, 114 mmol) in dichloro methane (200 mL) triethyl amine (17.4 mL, 125 mmol) was added. To this solution was then dropwise added benzoyl chloride (17.6 g, 125 mmol), followed by stirring at ambient temperature for 2 hours. The reaction was finally quenched by addition of dilute hydrochloric acid (50 mL, 10% HCl). The organic layer was separated, washed with water and dried over magnesium sulfate. Evaporation of the solvent yielded 31.5 g (99%) of the title compound as a dark oil.: The reaction was finally quenched by addition of dilute hydrochloric acid (50 mL, 10% HCl) The organic layer was separated washed with water dried over magnesium sulfate Evaporation of the solvent

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

实验步骤: Propionic acid chloride (2 mL, 2.1 g, 23 mmol) was added dropwise to a solution of indan-2-yl-propylamine (4.0 g, 23 mmol) and triethyl amine in dichloromethane (50 mL). The reaction mixture was stirred at room temperature for 2 hours. Aqueous (10%) sodium carbonate was added and the mixture was shaken. The organic phase was dried (magnesium sulfate), filtered and evaporated to yield 4.5 g (85%) of the title compound as an oil.: the mixture was shaken The organic phase was dried (magnesium sulfate) filtered evaporated

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

实验步骤: A tetrahydrofuran (150 mL) solution of 2-indanone (11.0 g, 92 mmol), propyl amine (12 mL, 146 mmol), sodium triacetoxy borohydride (35.0 g, 165 mmol), and acetic acid (5 mL) was stirred at ambient temperature for 1 hour. The solution was then heated at reflux temperature for 2 hours. After cooling, the solvent was evaporated and the residue taken up in concentrated hydrochloric acid (40 mL). The acidic solution was washed with diethyl ether and then basified (10M sodium hydroxide). Extraction of the aqueous layer with ether, drying over anhydrous sodium carbonate and removal of the solvent yielded 10.9 g of the title compound as a yellow oil (75%).: The solution was then heated at reflux temperature for 2 hours After cooling the solvent was evaporated The acidic solution was washed with diethyl ether Extraction of the aqueous layer with ether drying over anhydrous sodium carbonate and removal of the solvent

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

实验步骤: In 100 ml of tetrahydrofuran was suspended 5.7 g of lithium aluminum hydride, and to the suspension was added dropwise 18.9 g of 2-propionyl aminoindane dissolved in 150 ml of tetrahydrofuran. The mixture was refluxed under heating for 2 hours. After cooling, excessive lithium aluminum hydride was treated with a saturated ammonium chloride aqueous solution, and insolubles were removed by filtration. The filtrate was condensed, and chloroform was added to the residue. After the mixture was washed with 10 water and dried, the solvent was removed to obtain 17.5 g of 2-propylaminoindane. The mixture was refluxed under heating for 2 hours After cooling were removed by filtration condensed, and chloroform was added to the residue After the mixture was washed with 10 water dried the solvent was removed

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

实验步骤: 2-Propionamidoindan (24, 0.83 g, 4.4 mmol) was converted to 28 (0.75 g, 98%), as described for the reduction of 25. A small amount was converted to the hydrochloride and recrystallized from 2-propanol, which yielded white crystals: mp 191-192° C.; 1H-NMR (CDCl3, 200 MHz) 1.04 (t, J=7.3, 3H), 1.70-1.82 (m, 2H), 3.01-3.20 (m, 4H), 3.29-3.48 (m, 2H), 4.00-4.11 (m, 1H), 7.18-7.30 (m, 4H); 13C NMR 9.7, 19.3, 35.5 (2C), 47.6, 58.0, 124.2 (2C), 127.0 (2C), 138.6 (2C). HRMS calcd. (obsd.) for C12H17N 175.1361 (175.1364). recrystallized from 2-propanol, which yielded white crystals

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

实验步骤: In 100 ml of tetrahydrofuran was suspended 5.7 g of lithium aluminum hydride, and 150 ml of a solution containing 18.9 g of 2-(propionylamino) indane dissolved in tetrahydrofuran was added dropwise to the suspension. The mixture was refluxed under heating for 2 hours. After cooling, excess lithium aluminum hydride was treated with a saturated ammonium chloride aqueous solution, and insolubles were removed by filtration. The filtrate was concentrated, and chloroform was added to the residue. The mixture was washed with water and dried, and the solvent was removed to obtain 17.5 g of 2-(propylamino)indane. was added dropwise to the suspension The mixture was refluxed under heating for 2 hours After cooling were removed by filtration The filtrate was concentrated chloroform was added to the residue The mixture was washed with water dried the solvent was removed

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

实验步骤: In 100 ml of tetrahydrofuran was suspended 5.7 g of lithium aluminum hydride, and 150 ml of a solution containing 18.9 g of 2-(propionylamino) indane dissolved in tetrahydrofuran was added dropwise to the suspension. The mixture was refluxed under heating for 2 hours. After cooling, excess lithium aluminum hydride was treated with a saturated ammonium chloride aqueous solution, and insolubles were removed by filtration. The filtrate was concentrated, and chloroform was added to the residue. The mixture was washed with water and dried, and the solvent was removed to obtain 17.5 g of 2-(propylamino) indane. was added dropwise to the suspension The mixture was refluxed under heating for 2 hours After cooling were removed by filtration The filtrate was concentrated chloroform was added to the residue The mixture was washed with water dried the solvent was removed

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

实验步骤: To a solution of N-indan-2-yl-propylamine (9.5 g, 54.3 mmol) in methylene chloride was added aq. Na2CO3 (150 mL, 3%) followed by propionyl chloride (7.5 mL, 86.3 mmol). The mixture was stirred at ambient temperature for 1 h. The layers were separated and the organic layer was washed with water, separated and dried (MgSO4). Evaporation of the solvent yielded 7 g (56%) of N-indan-2-yl-N-propyl-propionamide. MS m/e 231 (1, M+), 116 (100), 117 (23), 57 (11), 146 (9). The layers were separated the organic layer was washed with water separated dried (MgSO4) Evaporation of the solvent