4-chloro-2,3-dihydro-1H-inden-1-amine

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

Procedure: To a solution of 4-chloro-indan-1-ylamine (390 mg) in diethyl ether (20 ml) was added 1-chloro-2-isothiocyanatoethane (283 mg) at 0° C. and the solution stirred for 2 h at the same temperature. The reaction mixture was quenched with diluted sodium hydroxide solution and extracted with diethyl ether. The residue was purified on silica gel to yield 240 mg of the product (41%). The reaction mixture was quenched with diluted sodium hydroxide solution extracted with diethyl ether The residue was purified on silica gel

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

Procedure: To a solution of 4-chloro-indan-1-ylamine (390 mg) in diethyl ether (20 ml) was added 1-chloro-2-isothiocyanatoethane (283 mg) at 0° C. and the solution stirred for 2 h at the same temperature. The reaction mixture was quenched with diluted sodium hydroxide solution and extracted with diethyl ether. The residue was purified on silica gel to yield 240 mg of the product (41%). The reaction mixture was quenched with diluted sodium hydroxide solution extracted with diethyl ether The residue was purified on silica gel

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

Procedure: A reaction mixture was prepared in a 250 ml. round bottom flask equipped with magnetic stirrer and drying tube containing the following ingredients: 32.5 g. of ammonium acetate, 2.67 g. of sodium cyanoborohydride (NaBH3CN), 70 ml. of tetrahydrofurane (THF), 60 ml. of methanol and 7 g. of 4-chloro-1-indanone. The reaction mixture was stirred at room temperature for about 48 hours. Thin-layer chromatography indicated only a trace of starting ketone remaining. The reaction mixture was cooled to below about 15° C. and acidified to pH = 2 with 12N aqueous hydrochloric acid. Volatile constituents were removed by evaporation in vacuo. The residue was taken up in water and the aqueous mixture extracted three times with ether. The ether extracts were discarded. The aqueous phase was then made basic with 5N aqueous sodium hydroxide and 4-chloro-1-aminoindane, formed in the above reaction, being insoluble in the alkaline layer separated and was extracted into ether. The ether layer was separated and the alkaline layer extracted twice more with ether. The ether extracts were combined, washed with saturated aqueous sodium chloride, and then dried. Evaporation of the ether in vacuo yielded 1.377 g. of an oily residue comprising 4-chloro-1-aminoindane. The hydrochloride salt was prepared by dissolving the residue in ether and passing gaseous hydrogenchloride through the ether solution. The resulting solid hydrochloride salt was separated by filtration. Recrystallization of the salt from a 3:1 isopropanol/ethyl acetate solvent mixture yielded 4-chloro-1-aminoindane hydrochloride melting above 250° C. (total yield = 641 mg.) A reaction mixture was prepared in a 250 ml round bottom flask equipped with magnetic stirrer drying tube containing the following ingredients The reaction mixture was cooled to below about 15° C. Volatile constituents were removed by evaporation in vacuo the aqueous mixture extracted three times with ether formed in the above reaction separated was extracted into ether The ether layer was separated the alkaline layer extracted twice more with ether washed with saturated aqueous sodium chloride dried Evaporation of the ether in vacuo yielded 1.377 g The resulting solid hydrochloride salt was separated by filtration Recrystallization of the salt from a 3:1 isopropanol/ethyl acetate solvent mixture

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

Procedure: To a solution of 4-chloro-indan-1-ylamine (390 mg) in diethyl ether (20 ml) was added 1-chloro-2-isothiocyanatoethane (283 mg) at 0° C. and the solution stirred for 2 h at the same temperature. The reaction mixture was quenched with diluted sodium hydroxide solution and extracted with diethyl ether. The residue was purified on silica gel to yield 240 mg of the product (41%). The reaction mixture was quenched with diluted sodium hydroxide solution extracted with diethyl ether The residue was purified on silica gel

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

Procedure: A reaction mixture was prepared in a 250 ml. round bottom flask equipped with magnetic stirrer and drying tube containing the following ingredients: 32.5 g. of ammonium acetate, 2.67 g. of sodium cyanoborohydride (NaBH3CN), 70 ml. of tetrahydrofurane (THF), 60 ml. of methanol and 7 g. of 4-chloro-1-indanone. The reaction mixture was stirred at room temperature for about 48 hours. Thin-layer chromatography indicated only a trace of starting ketone remaining. The reaction mixture was cooled to below about 15° C. and acidified to pH = 2 with 12N aqueous hydrochloric acid. Volatile constituents were removed by evaporation in vacuo. The residue was taken up in water and the aqueous mixture extracted three times with ether. The ether extracts were discarded. The aqueous phase was then made basic with 5N aqueous sodium hydroxide and 4-chloro-1-aminoindane, formed in the above reaction, being insoluble in the alkaline layer separated and was extracted into ether. The ether layer was separated and the alkaline layer extracted twice more with ether. The ether extracts were combined, washed with saturated aqueous sodium chloride, and then dried. Evaporation of the ether in vacuo yielded 1.377 g. of an oily residue comprising 4-chloro-1-aminoindane. The hydrochloride salt was prepared by dissolving the residue in ether and passing gaseous hydrogenchloride through the ether solution. The resulting solid hydrochloride salt was separated by filtration. Recrystallization of the salt from a 3:1 isopropanol/ethyl acetate solvent mixture yielded 4-chloro-1-aminoindane hydrochloride melting above 250° C. (total yield = 641 mg.) A reaction mixture was prepared in a 250 ml round bottom flask equipped with magnetic stirrer drying tube containing the following ingredients The reaction mixture was cooled to below about 15° C. Volatile constituents were removed by evaporation in vacuo the aqueous mixture extracted three times with ether formed in the above reaction separated was extracted into ether The ether layer was separated the alkaline layer extracted twice more with ether washed with saturated aqueous sodium chloride dried Evaporation of the ether in vacuo yielded 1.377 g The resulting solid hydrochloride salt was separated by filtration Recrystallization of the salt from a 3:1 isopropanol/ethyl acetate solvent mixture