N,N-dimethyl-2-phenylacetamide

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

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

Procedure: To a mechanically-stirred, refluxing suspension of 5.85 g (0.15 mol) of NaNH2 in 150 ml of toluene, was added dropwise under N2, 50 ml of a toluene solution consisting of 16.3 g (0.1 mol) of N,N-dimethyl-phenylacetamide (prepared by reaction of phenylacetyl chloride and N,N-dimethylamine in CH2Cl2 solvent) in toluene, and the mixture was stirred at reflux for 4 hr. Then, 16.5g (0.15 mol) of 2-(dimethylamino)ethyl chloride in 100 ml of toluene was added dropwise. The mixture was refluxed for 6 hr and then stirred at RT for 16 hr. Water (150 ml) was added to the mixture, and then the organic layer was separated and extracted with 1N HCl. The acid extract was basified in the cold with 2.5N NaOH and the basic solution extracted with Et2O. The ether extract was dried (Na2SO4), concentrated, and distilled to afford 18 g (76.8%) of N,N-dimethyl-4-dimethylamino-2-phenylbutanamide as a colorless oil, bp 108°-110°/0.2 mm. To a mechanically-stirred, refluxing was added dropwise under N2 at reflux for 4 hr The mixture was refluxed for 6 hr stirred at RT for 16 hr the organic layer was separated extracted with 1N HCl The acid extract the basic solution extracted with Et2O The ether extract was dried (Na2SO4) concentrated distilled

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

Procedure: In 204 ml of anhydrous benzene was dissolved 77.5 g (0.5 mole) of commercially available phenylacetyl chloride, and the solution was added dropwise to a 50% aqueous solution of 180 g (2.0 moles) of dimethyl amine, 50 g of ice and 100 ml of benzene at an inner temperature of 5° to 25° C. After completion of the dropwise addition, the mixture was agitated for 1 hour at the same temperature. After completion of the dropwise addition

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

Procedure: In 204 ml of anhydrous benzene was dissolved 77.5 g (0.5 mole) of commercially available phenylacetyl chloride, and the solution was added dropwise to a 50% aqueous solution of 180 g (2.0 moles) of dimethyl amine, 50 g of ice and 100 ml of benzene at an inner temperature of 5° to 25° C. After completion of the dropwise addition, the mixture was agitated for 1 hour at the same temperature. After completion of the dropwise addition

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

Procedure: To a mechanically-stirred, refluxing suspension of 5.85 g (0.15 mol) of NaNH2 in 150 ml of toluene, was added dropwise under N2, 50 ml of a toluene solution consisting of 16.3 g (0.1 mol) of N,N-dimethyl-phenylacetamide (prepared by reaction of phenylacetyl chloride and N,N-dimethylamine in CH2Cl2 solvent) in toluene, and the mixture was stirred at reflux for 4 hr. Then, 16.5g (0.15 mol) of 2-(dimethylamino)ethyl chloride in 100 ml of toluene was added dropwise. The mixture was refluxed for 6 hr and then stirred at RT for 16 hr. Water (150 ml) was added to the mixture, and then the organic layer was separated and extracted with 1N HCl. The acid extract was basified in the cold with 2.5N NaOH and the basic solution extracted with Et2O. The ether extract was dried (Na2SO4), concentrated, and distilled to afford 18 g (76.8%) of N,N-dimethyl-4-dimethylamino-2-phenylbutanamide as a colorless oil, bp 108°-110°/0.2 mm. To a mechanically-stirred, refluxing was added dropwise under N2 at reflux for 4 hr The mixture was refluxed for 6 hr stirred at RT for 16 hr the organic layer was separated extracted with 1N HCl The acid extract the basic solution extracted with Et2O The ether extract was dried (Na2SO4) concentrated distilled

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

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

Procedure: To a mechanically-stirred, refluxing suspension of 5.85 g (0.15 mol) of NaNH2 in 150 ml of toluene, was added dropwise under N2, 50 ml of a toluene solution consisting of 16.3 g (0.1 mol) of N,N-dimethyl-phenylacetamide (prepared by reaction of phenylacetyl chloride and N,N-dimethylamine in CH2Cl2 solvent) in toluene, and the mixture was stirred at reflux for 4 hr. Then, 16.5 g (0.15 mol) of 2-(dimethylamino)ethyl chloride in 100 ml of toluene was added dropwise. The mixture was refluxed for 6 hr and then stirred at RT for 16 hr. Water (150 ml) was added to the mixture, and then the organic layer was separated and extracted with 1N HCl. The acid extract was basified in the cold with 2.5N NaOH and the basic solution extracted with Et2O. The ether extract was dried (Na2SO4), concentrated, and distilled to afford 18 g (76.8%) of N,N-dimethyl-4-dimethylamino-2-phenylbutanamide as a colorless oil, bp 108°-110°/0.2 mm. To a mechanically-stirred, refluxing was added dropwise under N2 at reflux for 4 hr The mixture was refluxed for 6 hr stirred at RT for 16 hr the organic layer was separated extracted with 1N HCl The acid extract the basic solution extracted with Et2O The ether extract was dried (Na2SO4) concentrated distilled

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

Procedure: To a mechanically-stirred, refluxing suspension of 5.85 g (0.15 mol) of NaNH2 in 150 ml of toluene, was added dropwise under N2, 50 ml of a toluene solution consisting of 16.3 g (0.1 mol) of N,N-dimethyl-phenylacetamide (prepared by reaction of phenylacetyl chloride and N,N-dimethylamine in CH2Cl2 solvent) in toluene, and the mixture was stirred at reflux for 4 hr. Then, 16.5 g (0.15 mol) of 2-(dimethylamino)ethyl chloride in 100 ml of toluene was added dropwise. The mixture was refluxed for 6 hr and then stirred at RT for 16 hr. Water (150 ml) was added to the mixture, and then the organic layer was separated and extracted with 1N HCl. The acid extract was basified in the cold with 2.5N NaOH and the basic solution extracted with Et2O. The ether extract was dried (Na2SO4), concentrated, and distilled to afford 18 g (76.8%) of N,N-dimethyl-4-dimethylamino-2-phenylbutanamide as a colorless oil, bp 108°-110°/0.2 mm. To a mechanically-stirred, refluxing was added dropwise under N2 at reflux for 4 hr The mixture was refluxed for 6 hr stirred at RT for 16 hr the organic layer was separated extracted with 1N HCl The acid extract the basic solution extracted with Et2O The ether extract was dried (Na2SO4) concentrated distilled

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyllithium in diethyl ether (140 ml of 1.8 M solution, 0.25 mol) was added dropwise to a solution of 27.6 g (0.27 mol) of diisopropylamine in 40 ml of dry diethyl ether. The reaction mixture was cooled to -70° C. and a solution of 26.1 g (0.16 mol) of N,N-dimethylbenzeneacetamide in 75 ml of diethyl ether was added dropwise. The reaction mixture was warmed to 0° C. and 46 ml (0.36 mol) of trimethylchlorosilane were added dropwise. The reaction mixture was stirred at 25° C. overnight, the solid was filtered off, and the filtrate was distilled to give 7.65 g of β-(N,N-dimethylamino)-β-trimethylsiloxystyrene as a light yellow oil: bp 75°-78° C. (0.5 mm); 1H NMR (CDCl3) δ 2.18 ppm (s, 6H), 4.83 ppm (s, 1H), 6.7-7.6 ppm (m, 5H) and 0.04 ppm (s, 9H). Anal. Calcd. for C13H21NOSi: C, 66.33; H, 8.99; N, 5.95; Found: C, 66.47; H, 9.11; N, 5.78. The reaction mixture was warmed to 0° C. the solid was filtered off the filtrate was distilled

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

Procedure: Phenylacetyl chloride (25 ml) was added dropwise to a 50% aqueous solution of dimethylamine with ice-cooling. After the solvent was removed under reduced pressure, the residue was dissolved in ethyl acetate. The organic layer was washed with saturated aqueous NaHCO3 solution, dried over MgSO4, and concentrated under reduced pressure to provide the title compound as colorless oil. Yield 28.90 g (95%) 1H-NMR (CDCl3) δ: 2.95(3H,s), 2.98(3H,s), 3.71(2H,s), 7.26-7.30(5H,m). cooling After the solvent was removed under reduced pressure the residue was dissolved in ethyl acetate The organic layer was washed with saturated aqueous NaHCO3 solution dried over MgSO4 concentrated under reduced pressure

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

Procedure: In 204 ml of anhydrous benzene was dissolved 77.5 g (0.5 mole) of commercially available phenylacetyl chloride, and the solution was added dropwise to a 50% aqueous solution of 180 g (2.0 moles) of dimethyl amine, 50 g of ice and 100 ml of benzene at an inner temperature of 5° to 25° C. After completion of the dropwise addition, the mixture was agitated for 1 hour at the same temperature. After completion of the dropwise addition

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

Procedure: To a mechanically-stirred, refluxing suspension of 5.85 g (0.15 mol) of NaNH2 in 150 ml of toluene, was added dropwise under N2, 50 ml of a toluene solution consisting of 16.3 g (0.1 mol) of N,N-dimethyl-phenylacetamide (prepared by reaction of phenylacetyl chloride and N,N-dimethylamine in CH2Cl2 solvent) in toluene, and the mixture was stirred at reflux for 4 hr. Then, 16.5g (0.15 mol) of 2-(dimethylamino)ethyl chloride in 100 ml of toluene was added dropwise. The mixture was refluxed for 6 hr and then stirred at RT for 16 hr. Water (150 ml) was added to the mixture, and then the organic layer was separated and extracted with 1N HCl. The acid extract was basified in the cold with 2.5N NaOH and the basic solution extracted with Et2O. The ether extract was dried (Na2SO4), concentrated, and distilled to afford 18 g (76.8%) of N,N-dimethyl-4-dimethylamino-2-phenylbutanamide as a colorless oil, bp 108°-110°/0.2 mm. To a mechanically-stirred, refluxing was added dropwise under N2 at reflux for 4 hr The mixture was refluxed for 6 hr stirred at RT for 16 hr the organic layer was separated extracted with 1N HCl The acid extract the basic solution extracted with Et2O The ether extract was dried (Na2SO4) concentrated distilled