2-[(2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]ethanamine

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.5 g of magnesium sulfate are added to a solution of 3-cyclopenten-1-ylbenzaldehyde (2a) (0.56 g, 3.26 mmol) and of [2-(2,2-dimethyl-2,3-dihydrobenzofuran-7-yl-oxy)]ethylamine (3a) (0.68 g, 3.26 mmol) in 15 ml of 1,2-dichloroethane and the mixture is heated at 60° C. for 17 hours. The mixture is cooled to room temperature, the solid is filtered and the solvent is evaporated under reduced pressure. The residue is diluted with 15 ml of methanol and then cooled to 0° C. 0.35 g of potassium borohydride (6.52 mmol) is then introduced and the reaction mixture is stirred for 3 hours at 0° C. The mixture is then poured into ice-cold water, extracted with ethyl acetate and washed with a saturated aqueous sodium chloride solution. The combined organic phases are dried over magnesium sulfate, filtered and the solvent is evaporated under reduced pressure. The residue is purified by chromatography on silica gel (methylene chloride/methanol/aqueous ammonia: 98/1.5/0.5). The title product (0.61 g) is isolated in the form of a colorless oil. The mixture is cooled to room temperature the solid is filtered the solvent is evaporated under reduced pressure The residue is diluted with 15 ml of methanol cooled to 0° C The mixture is then poured into ice-cold water extracted with ethyl acetate washed with a saturated aqueous sodium chloride solution The combined organic phases are dried over magnesium sulfate filtered the solvent is evaporated under reduced pressure The residue is purified by chromatography on silica gel (methylene chloride/methanol/aqueous ammonia: 98/1.5/0.5)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.5 g of magnesium sulfate are added to a solution of 3-cyclopenten-1-ylbenzaldehyde (2a) (0.56 g, 3.26 mmol) and of [2-(2,2-dimethyl-2,3-dihydrobenzofuran-7-yl-oxy)]ethylamine (3a) (0.68 g, 3.26 mmol) in 15 ml of 1,2-dichloroethane and the mixture is heated at 60° C. for 17 hours. The mixture is cooled to room temperature, the solid is filtered and the solvent is evaporated under reduced pressure. The residue is diluted with 15 ml of methanol and then cooled to 0° C. 0.35 g of potassium borohydride (6.52 mmol) is then introduced and the reaction mixture is stirred for 3 hours at 0° C. The mixture is then poured into ice-cold water, extracted with ethyl acetate and washed with a saturated aqueous sodium chloride solution. The combined organic phases are dried over magnesium sulfate, filtered and the solvent is evaporated under reduced pressure. The residue is purified by chromatography on silica gel (methylene chloride/methanol/aqueous ammonia: 98/1.5/0.5). The title product (0.61 g) is isolated in the form of a colorless oil. The mixture is cooled to room temperature the solid is filtered the solvent is evaporated under reduced pressure The residue is diluted with 15 ml of methanol cooled to 0° C The mixture is then poured into ice-cold water extracted with ethyl acetate washed with a saturated aqueous sodium chloride solution The combined organic phases are dried over magnesium sulfate filtered the solvent is evaporated under reduced pressure The residue is purified by chromatography on silica gel (methylene chloride/methanol/aqueous ammonia: 98/1.5/0.5)