N-methyl-2-phenylacetamide

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

Procedure: To 7.46 g (0.05 mol) of N-methyl phenylacetamide (prepared by reaction of phenylacetyl chloride with monomethylamine in CH2Cl2 solvent) dissolved in 70 ml of THF and cooled in an ice-bath to 0°, was added dropwise with stirring under N2, 40 ml (0.10 mol) of a 2.5M solution of N-BuLi in n-hexane. After stirring at 0° for 30 min, the solution was treated by the rapid addition of 5.4 g (0.05 mol) of 2-(dimethylamino)ethyl chloride in 30 ml of THF and then stirred at 0° for 30 min. The reaction mixture was then poured into 250 ml of 1N HCl, ether was added and the aqueous layer was separated, basified with 2.5N NaOH and extracted with Et2O. The ether extract was dried (Na2SO4), concentrated, and kugelrohr distilled to afford 9.2 g (83.5%) of N-methyl-4-dimethylamino-2-phenylbutanamide as a viscous. colorless oil; bp 130°-135°/0.1 mm. cooled in an ice-bath to 0° was added dropwise After stirring at 0° for 30 min stirred at 0° for 30 min was added the aqueous layer was separated extracted with Et2O The ether extract was dried (Na2SO4) concentrated kugelrohr distilled

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

Procedure: To 7.46 g (0.05 mol) of N-methyl phenylacetamide (prepared by reaction of phenylacetyl chloride with monomethylamine in CH2Cl2 solvent) dissolved in 70 ml of THF and cooled in an ice-bath to 0°, was added dropwise with stirring under N2, 40 ml (0.10 mol) of a 2.5M solution of N-BuLi in n-hexane. After stirring at 0° for 30 min, the solution was treated by the rapid addition of 5.4 g (0.05 mol) of 2-(dimethylamino)ethyl chloride in 30 ml of THF and then stirred at 0° for 30 min. The reaction mixture was then poured into 250 ml of 1N HCl, ether was added and the aqueous layer was separated, basified with 2.5N NaOH and extracted with Et2O. The ether extract was dried (Na2SO4), concentrated, and kugelrohr distilled to afford 9.2 g (83.5%) of N-methyl-4-dimethylamino-2-phenylbutanamide as a viscous. colorless oil; bp 130°-135°/0.1 mm. cooled in an ice-bath to 0° was added dropwise After stirring at 0° for 30 min stirred at 0° for 30 min was added the aqueous layer was separated extracted with Et2O The ether extract was dried (Na2SO4) concentrated kugelrohr distilled

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

Procedure: To 7.46 g (0.05 mol) of N-methyl phenylacetamide (prepared by reaction of phenylacetyl chloride with monomethylamine in CH2Cl2 solvent) dissolved in 70 ml of THF and cooled in an ice-bath to 0°, was added dropwise with stirring under N2, 40 ml (0.10 mol) of a 2.5M solution of N-BuLi in n-hexane. After stirring at 0° for 30 min, the solution was treated by the rapid addition of 5.4 g (0.05 mol) of 2-(dimethylamino)ethyl chloride in 30 ml of THF and then stirred at 0° for 30 min. The reaction mixture was then poured into 250 ml of 1N HCl, ether was added and the aqueous layer was separated, basified with 2.5N NaOH and extracted with Et2O. The ether extract was dried (Na2SO4), concentrated, and kugelrohr distilled to afford 9.2 g (83.5%) of N-methyl-4-dimethylamino-2-phenylbutanamide as a viscous, colorless oil; bp 130°-135°/0.1 mm. cooled in an ice-bath to 0° was added dropwise After stirring at 0° for 30 min stirred at 0° for 30 min was added the aqueous layer was separated extracted with Et2O The ether extract was dried (Na2SO4) concentrated kugelrohr distilled

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

Procedure: To 7.46 g (0.05 mol) of N-methyl phenylacetamide (prepared by reaction of phenylacetyl chloride with monomethylamine in CH2Cl2 solvent) dissolved in 70 ml of THF and cooled in an ice-bath to 0°, was added dropwise with stirring under N2, 40 ml (0.10 mol) of a 2.5M solution of N-BuLi in n-hexane. After stirring at 0° for 30 min, the solution was treated by the rapid addition of 5.4 g (0.05 mol) of 2-(dimethylamino)ethyl chloride in 30 ml of THF and then stirred at 0° for 30 min. The reaction mixture was then poured into 250 ml of 1N HCl, ether was added and the aqueous layer was separated, basified with 2.5N NaOH and extracted with Et2O. The ether extract was dried (Na2SO4), concentrated, and kugelrohr distilled to afford 9.2 g (83.5%) of N-methyl-4-dimethylamino-2-phenylbutanamide as a viscous, colorless oil; bp 130°-135°/0.1 mm. cooled in an ice-bath to 0° was added dropwise After stirring at 0° for 30 min stirred at 0° for 30 min was added the aqueous layer was separated extracted with Et2O The ether extract was dried (Na2SO4) concentrated kugelrohr distilled

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

Procedure: Dissolved 15 g(0.1 mol) of phenylacetyl chloride in 100 ml of benzene. While stirring on a magnetic stirrer, introduced methylamine into the benzene solution at 20°-30° C. Followed the procedure of compound 3-1 for the purification of the product to yield N-methyl phenylacetamide as light yellowish crystal. Yield, 12 g (80%). Followed the procedure of compound 3-1 for the purification of the product

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

Procedure: Phenylacetic acid (10 g, 73.5 mmol) and methanol (60 ml) were added to a 250 ml three-necked flask, followed by addition of 10 drops concentrated sulphuric acid. The resulting solution was heated to reflux for 2 hours. Then, the solution was cooled to room temperature, followed by adding 25-30% aqueous solution of methylamine (50 ml, approximately 403 mmol), and heated to reflux for another 3 hours. After the reaction was completed, it was cooled to room temperature. Most of the solvent was removed by rotary vacuum evaporation, 30 ml of water was added thereinto, and then the mixture was extracted with ethyl acetate (3×80 ml). The combined organic layer was dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure to yield 10.1 g of N-methyl phenylacetamide (white solid, yield: 91.8%). The resulting solution was heated to reflux for 2 hours heated to reflux for another 3 hours it was cooled to room temperature Most of the solvent was removed by rotary vacuum evaporation, 30 ml of water was added the mixture was extracted with ethyl acetate (3×80 ml) The combined organic layer was dried over anhydrous magnesium sulfate filtrated concentrated under reduced pressure

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

Procedure: To 7.46 g (0.05 mol) of N-methyl phenylacetamide (prepared by reaction of phenylacetyl chloride with monomethylamine in CH2Cl2 solvent) dissolved in 70 ml of THF and cooled in an ice-bath to 0°, was added dropwise with stirring under N2, 40 ml (0.10 mol) of a 2.5M solution of N-BuLi in n-hexane. After stirring at 0° for 30 min, the solution was treated by the rapid addition of 5.4 g (0.05 mol) of 2-(dimethylamino)ethyl chloride in 30 ml of THF and then stirred at 0° for 30 min. The reaction mixture was then poured into 250 ml of 1N HCl, ether was added and the aqueous layer was separated, basified with 2.5N NaOH and extracted with Et2O. The ether extract was dried (Na2SO4), concentrated, and kugelrohr distilled to afford 9.2 g (83.5%) of N-methyl-4-dimethylamino-2-phenylbutanamide as a viscous. colorless oil; bp 130°-135°/0.1 mm. cooled in an ice-bath to 0° was added dropwise After stirring at 0° for 30 min stirred at 0° for 30 min was added the aqueous layer was separated extracted with Et2O The ether extract was dried (Na2SO4) concentrated kugelrohr distilled