2-(3,4-dimethoxyphenyl)acetamide

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

Procedure: The title compound was prepared using the method of Example 2b after substituting an equivalent amount of methylurea for (3,4-dimethoxyphenyl)acetamide as a starting material and diluting the solution three-fold with benzene. The crude product was purified by silica gel flash chromatography eluting with a 25% ethyl acetate/hexane solution. The eluate was evaporated in vacuo to yield the title compound as a white solid, mp 129°-131° C. The title compound was prepared The crude product was purified by silica gel flash chromatography eluting with a 25% ethyl acetate/hexane solution The eluate was evaporated in vacuo

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

Procedure: The title compound was prepared using the method of Example 2b after substituting equivalent quantities of benzamide for (3,4-dimethoxyphenyl)acetamide and 3,3-diphenylglutaraldehyde (the compound of Example 4a) for 3,3-dimethylglutaraldehyde as starting materials. The crude product was purified by silica gel flash chromatography eluting with a 7% ethyl acetate/hexane solution. The eluate was evaporated in vacuo to yield a clear oil which, after triturating with methanol, gave the title compound as a white solid, mp 91°-93° C. The title compound was prepared The crude product was purified by silica gel flash chromatography eluting with a 7% ethyl acetate/hexane solution The eluate was evaporated in vacuo to yield a clear oil which after triturating with methanol

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

Procedure: To a solution of 35.31 g (0.18 mole) of (3,4-dimethoxyphenyl)acetic acid in 345 ml of dry toluene and 34.5 ml of dry DMF at 0° C. under argon was added 16.8 ml (0.19 mole) of freshly distilled oxalyl chloride over 40 minutes. The reaction was stirred an additional 35 minutes at 0° C. and then at room temperature for 17 hours. The reaction mixture was again cooled to 0° C. and gaseous ammonia slowly bubbled through it for 1 hour. The reaction mixture was warmed to room temperature and stirred for 4 hours after which the solid was filtered off and partitioned between chloroform and water. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo giving 20.84 g of the title compound as an off-white solid, mp 142°-144° C. at room temperature for 17 hours The reaction mixture was again cooled to 0° C. gaseous ammonia slowly bubbled through it for 1 hour The reaction mixture was warmed to room temperature stirred for 4 hours after which the solid was filtered off partitioned between chloroform and water The organic phase was washed with brine dried over anhydrous magnesium sulfate filtered evaporated in vacuo