N,N-diethyl-2,3-dihydro-1H-inden-2-amine

Conditions: temp:7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of Example 226A (2.0 g, 10.57 mmol) in trifluoroacetic acid (80 ml, 1038 mmol) was added nitric acid (0.726 ml, 10.57 mmol) dropwise at 0° C. The mixture was stirred at 0-15° C. for 5 hours. The solution was poured into ice/water (20 mL) and the pH was adjusted to 10 with NH3/H2O. The mixture was extracted with methylene chloride (4×50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to provide the title compound. The mixture was extracted with methylene chloride (4×50 mL) The combined organic layers were dried over Na2SO4 filtered concentrated

Conditions: temp:7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of Example 226A (2.0 g, 10.57 mmol) in trifluoroacetic acid (80 ml, 1038 mmol) was added nitric acid (0.726 ml, 10.57 mmol) dropwise at 0° C. The mixture was stirred at 0-15° C. for 5 hours. The solution was poured into ice/water (20 mL) and the pH was adjusted to 10 with NH3/H2O. The mixture was extracted with methylene chloride (4×50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to provide the title compound. The mixture was extracted with methylene chloride (4×50 mL) The combined organic layers were dried over Na2SO4 filtered concentrated

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

Procedure: To a solution of 1H-inden-2(3H)-one (6.00 g, 45.4 mmol) in methanol (100 ml) was added diethylamine (6.64 g, 91 mmol), sodium cyanotrihydroborate (5.71 g, 91 mmol) and acetic acid (5.45 g, 91 mmol). The reaction mixture was stirred overnight and concentrated. The residue was diluted with methylene chloride, washed with saturated aqueous NaHCO3 (2×50 mL), dried over Na2SO4, filtered, and concentrated. The resulting residue was dissolved in 1M aqueous HCl (100 ml), and extracted with methylene chloride (2×50 mL). The aqueous layer was treated with 6N aqueous NaOH solution until the pH=14 and was extracted with methylene chloride (4×100 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to provide the title compound. concentrated The residue was diluted with methylene chloride washed with saturated aqueous NaHCO3 (2×50 mL) dried over Na2SO4 filtered concentrated The resulting residue was dissolved in 1M aqueous HCl (100 ml) extracted with methylene chloride (2×50 mL) The aqueous layer was treated with 6N aqueous NaOH solution until the pH=14 was extracted with methylene chloride (4×100 mL) The combined organic layers were dried over Na2SO4 filtered concentrated

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

Procedure: To a solution of 1H-inden-2(3H)-one (6.00 g, 45.4 mmol) in methanol (100 ml) was added diethylamine (6.64 g, 91 mmol), sodium cyanotrihydroborate (5.71 g, 91 mmol) and acetic acid (5.45 g, 91 mmol). The reaction mixture was stirred overnight and concentrated. The residue was diluted with methylene chloride, washed with saturated aqueous NaHCO3 (2×50 mL), dried over Na2SO4, filtered, and concentrated. The resulting residue was dissolved in 1M aqueous HCl (100 ml), and extracted with methylene chloride (2×50 mL). The aqueous layer was treated with 6N aqueous NaOH solution until the pH=14 and was extracted with methylene chloride (4×100 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to provide the title compound. concentrated The residue was diluted with methylene chloride washed with saturated aqueous NaHCO3 (2×50 mL) dried over Na2SO4 filtered concentrated The resulting residue was dissolved in 1M aqueous HCl (100 ml) extracted with methylene chloride (2×50 mL) The aqueous layer was treated with 6N aqueous NaOH solution until the pH=14 was extracted with methylene chloride (4×100 mL) The combined organic layers were dried over Na2SO4 filtered concentrated