4-(2-methoxyphenyl)-2-methylbutan-2-amine

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: 6.0 g (0.023 mole) of 3,4-dihydro-6-bromoacetylquinolin-2(1H)-one, 4.8 g (0.025 mole) of 1,1-dimethyl-3-(2-methoxy-phenyl)-propanamine and 3.2 g (0.03 mole) of potassium carbonate are stirred in 100 ml of dimethylformamide at room temperature for 24 hours. After dilution with methanol, the product is reduced with an excess of sodium borohydride. The solvents are removed in vacuo, the residue is taken up in methylene chloride and the mixture is extracted with water. Column chromatography on silica gel (CHCl3 /MeOH 90/10) gives 3,4-dihydro-6-[1-hydroxy-2-[[1,1-dimethyl-3-(2-methoxy-phenyl)-propyl]-amino]-ethyl]-quinolin-2(1H)-one as a base, which is converted into the hydrochloride in the customary manner. Melting point 180° C. (decomposition). The solvents are removed in vacuo the mixture is extracted with water

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

Procedure: To a cold (0° C.) solution of 986 mg (5.1 mmol) of 2-amino-2-methyl-4-(2-methoxyphenyl)butane in 20 ml of dry methylene chloride, a solution of 2.5 ml of a 1M BBr3 solution in 10 ml of methylene chloride is slowly added. The reaction mixture is stirred at 0° C. for two hours and then at room temperature for 3 hours. The reaction is quenched with methanol and concentrated. Pure product may be obtained by chromatography on silica gel. at room temperature for 3 hours The reaction is quenched with methanol concentrated Pure product may be obtained by chromatography on silica gel

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