N-methyl-2,3-dihydro-1H-indene-1-carboxamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 4.0 g (0.1M) of LAH and 400 ml of ether was stirred while a solution of 9.0 g (51 mmol) of 1-methylaminocarbonyl-indane, a compound of Formula 13 prepared, for example, as described in Preparation 13, dissolved 200 ml of THF was added over a period of 30 minutes. The reaction mixture was stirred and heated to reflux for 6 hours, and then stirred at ambient temperature for an additional 16 hours. The reaction mixture was then digested by treating dropwise with water, 15% NaOH, and then water, yielding 1-methylaminomethyl-indane, an intermediate amine of Formula 14; (HCl salt, ethanol-ether, mp 169°-171° C.). as described in Preparation 13 was added over a period of 30 minutes heated to reflux for 6 hours stirred at ambient temperature for an additional 16 hours

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

Procedure: A mixture of 150 ml of ethyl acetate and 50 ml of 40% aqueous methylamine (approx. 0.5M) was stirred in an ice bath, while a solution of 11.7 g (65 mmol) of indane-1-carboxylic acid chloride, a compound of Formula 4 prepared, for example, as described in Preparation 4, dissolved 40 ml of ethyl acetate was added over a period of 15 minutes. Stirring was continued at ambient temperature for an additional 4 hours. The organic layer is separated, washed three times with water, once with 10% HCl, and once with saturated sodium bicarbonate. Evaporation of the ethyl acetate yielded 9.0 g of 1-methylaminocarbonyl-indane, an amide of Formula 13; (mp 107°-109° C.; ir 1635 cm-1). as described in Preparation 4 was added over a period of 15 minutes The organic layer is separated washed three times with water Evaporation of the ethyl acetate

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

Procedure: A mixture of 150 ml of ethyl acetate and 50 ml of 40% aqueous methylamine (approx. 0.5M) was stirred in an ice bath, while a solution of 11.7 g (65 mmol) of indane-1-carboxylic acid chloride, a compound of Formula 4 prepared, for example, as described in Preparation 4, dissolved 40 ml of ethyl acetate was added over a period of 15 minutes. Stirring was continued at ambient temperature for an additional 4 hours. The organic layer is separated, washed three times with water, once with 10% HCl, and once with saturated sodium bicarbonate. Evaporation of the ethyl acetate yielded 9.0 g of 1-methylaminocarbonyl-indane, an amide of Formula 13; (mp 107°-109° C.; ir 1635 cm-1). as described in Preparation 4 was added over a period of 15 minutes The organic layer is separated washed three times with water Evaporation of the ethyl acetate

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

Procedure: A mixture of 4.0 g (0.1M) of LAH and 400 ml of ether was stirred while a solution of 9.0 g (51 mmol) of 1-methylaminocarbonyl-indane, a compound of Formula 13 prepared, for example, as described in Preparation 13, dissolved 200 ml of THF was added over a period of 30 minutes. The reaction mixture was stirred and heated to reflux for 6 hours, and then stirred at ambient temperature for an additional 16 hours. The reaction mixture was then digested by treating dropwise with water, 15% NaOH, and then water, yielding 1-methylaminomethyl-indane, an intermediate amine of Formula 14; (HCl salt, ethanol-ether, mp 169°-171° C.). as described in Preparation 13 was added over a period of 30 minutes heated to reflux for 6 hours stirred at ambient temperature for an additional 16 hours

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

Procedure: A mixture of 150 ml of ethyl acetate and 50 ml of 40% aqueous methylamine (approx. 0.5M) was stirred in an ice bath, while a solution of 11.7 g (65 mmol) of indane-1-carboxylic acid chloride, a compound of Formula 4 prepared, for example, as described in Preparation 4, dissolved 40 ml of ethyl acetate was added over a period of 15 minutes. Stirring was continued at ambient temperature for an additional 4 hours. The organic layer is separated, washed three times with water, once with 10% HCl, and once with saturated sodium bicarbonate. Evaporation of the ethyl acetate yielded 9.0 g of 1-methylaminocarbonyl-indane, an amide of Formula 13; (mp 107°-109° C.; ir 1635 cm-1). as described in Preparation 4 was added over a period of 15 minutes The organic layer is separated washed three times with water Evaporation of the ethyl acetate