1-(2,3-dihydro-1H-inden-2-yl)ethanone

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled solution of 3.5 g (21.8 mmol) of 1-(indan-2-yl)ethanone in 100 ml of methanol, are added 10 g of 3 Å molecular sieves and 2.3 g (40.2 mmol) of cyclopropylamine followed by a slow addition of 2.87 ml (50.2 mmol) of acetic acid. The reaction mixture is stirred for 2.5 hrs at reflux. The reaction mixture is then cooled to 0° C. and 1.9 g (30 mmol) of sodium cyanoborohydride are slowly added and the reaction mixture is further stirred for 2 hrs at reflux. The cooled reaction mixture is then filtered over a cake of diatomaceous earth. The cake is washed twice by 80 ml of methanol and the combined methanolic extracts are concentrated under vacuum. 100 ml of water are then added to the residue and the pH is ajusted to 12 with a 0.5 N solution of sodium hydroxyde. The watery layer is extracted with 300 ml of ethyl acetate. The organic layer is washed twice by brine and filtered over a phase separator paper to yield after concentration 5 g of a yellow oil. Column chromatography on silica gel (gradient heptane/ethyl acetate) yields 1.2 g (28% yield) of N-[1-(indan-2-yl)ethyl]cyclopropanamine as a colourless oil (M+H =202). at reflux the reaction mixture is further stirred for 2 hrs at reflux The cooled reaction mixture is then filtered over a cake of diatomaceous earth The cake is washed twice by 80 ml of methanol the combined methanolic extracts are concentrated under vacuum 100 ml of water are then added to the residue The watery layer is extracted with 300 ml of ethyl acetate The organic layer is washed twice by brine filtered over a phase separator paper to yield after concentration 5 g of a yellow oil

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

Procedure: 10 g of pure bromine are rapidly added at 0° C. to a solution of 10 g of 2-acetylindane in 150 ml of anhydrous methanol. After one hour at ambient temperature, 100 ml of water are added and the whole is stirred for 12 hours. After extracting twice with 200 ml of diethyl ether each time, and washing the organic phase with a sodium hydrogen carbonate solution and then with water, the expected product is dried over magnesium sulphate and concentrated. After extracting twice with 200 ml of diethyl ether each time washing the organic phase with a sodium hydrogen carbonate solution with water, the expected product is dried over magnesium sulphate concentrated

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

Procedure: 1-(2,3-dihydro-1H-inden-2-yl)ethanone (44 mg, 0.275 mmol) was dissolved in methanol (2 mL), and 7 M methanolic ammonia was added (1 mL, 7 mmol). This was allowed to stir at rt for 4 h, at which time sodium borohydride (31 mg, 0.824 mmol) and a catalytic drop of glacial acetic acid was added. Stirring continued for 14 h at rt, after which time the solvent was removed in vacuo. The residue was taken up in ethyl acetate and washed with a small amount of 10% aqueous sodium carbonate, dried with magnesium sulfate, and concentrated. The residue was then taken on in subsequent reactions without further purification or characterization. after which time the solvent was removed in vacuo washed with a small amount of 10% aqueous sodium carbonate dried with magnesium sulfate concentrated The residue was then taken on in subsequent reactions without further purification or characterization

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

Procedure: Bromine (6.8 g) is slowly added to a stirred solution of 1-(2,3-dihydro-1H-inden-2-yl)ethanone (6.8 g) in 200 ml of dry ether, while keeping the temperature at +10° C. The rate of the addition of bromine is controlled so that the colour due to one added portion of bromine has been discharged before another portion is added. When the addition is complete, the ethereal solution is washed four times with 3M sodium carbonate solution, and is then washed three times with water. The ethereal solution is dried with anhydrous magnesium sulphate. After removal of the solvent the solid 2-bromo-1-(2,3-dihydro-1H-inden-2-yl)ethanone is obtained. at +10° C is added When the addition the ethereal solution is washed four times with 3M sodium carbonate solution is then washed three times with water The ethereal solution is dried with anhydrous magnesium sulphate After removal of the solvent the solid 2-bromo-1-(2,3-dihydro-1H-inden-2-yl)ethanone is obtained

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled solution of 3.5 g (21.8 mmol) of 1-(indan-2-yl)ethanone in 100 ml of methanol, are added 10 g of 3 Å molecular sieves and 2.3 g (40.2 mmol) of cyclopropylamine followed by a slow addition of 2.87 ml (50.2 mmol) of acetic acid. The reaction mixture is stirred for 2.5 hrs at reflux. The reaction mixture is then cooled to 0° C. and 1.9 g (30 mmol) of sodium cyanoborohydride are slowly added and the reaction mixture is further stirred for 2 hrs at reflux. The cooled reaction mixture is then filtered over a cake of diatomaceous earth. The cake is washed twice by 80 ml of methanol and the combined methanolic extracts are concentrated under vacuum. 100 ml of water are then added to the residue and the pH is ajusted to 12 with a 0.5 N solution of sodium hydroxyde. The watery layer is extracted with 300 ml of ethyl acetate. The organic layer is washed twice by brine and filtered over a phase separator paper to yield after concentration 5 g of a yellow oil. Column chromatography on silica gel (gradient heptane/ethyl acetate) yields 1.2 g (28% yield) of N-[1-(indan-2-yl)ethyl]cyclopropanamine as a colourless oil (M+H =202). at reflux the reaction mixture is further stirred for 2 hrs at reflux The cooled reaction mixture is then filtered over a cake of diatomaceous earth The cake is washed twice by 80 ml of methanol the combined methanolic extracts are concentrated under vacuum 100 ml of water are then added to the residue The watery layer is extracted with 300 ml of ethyl acetate The organic layer is washed twice by brine filtered over a phase separator paper to yield after concentration 5 g of a yellow oil