N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2-dimethylpropanamide

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

Procedure: Dissolve 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl]-2,2-dimethylpropionamide in 10 ml. of benzene and 15 g. of aluminum chloride. Reflux the mixture overnight (17 hours) with vigorous stirring. Cool the mixture to room temperature and, cautiously, pour the reaction mixture into dilute hydrochloric acid and ice with vigorous stirring. Separate the liquid phases and discard the benzene layer. Extract the aqueous layer with ethyl-acetate, then wash the extract with saturated sodium bicarbonate and water. Dry the extract over anhydrous sodium sulfate, filter and vaporate to a residue. Crystallize the residue from a 9:1 mixture of toluene:ethanol to obtain the title product. Dissolve 0.53 g Reflux the mixture overnight (17 hours) with vigorous stirring Separate the liquid phases Extract the aqueous layer with ethyl-acetate wash the extract with saturated sodium bicarbonate and water Dry the extract over anhydrous sodium sulfate filter Crystallize the residue from a 9:1 mixture of toluene

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

Procedure: Dissolve 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl]-2,2-dimethylpropionamide in 10 ml. of benzene and 15 g. of aluminum chloride. Reflux the mixture overnight (17 hours) with vigorous stirring. Cool the mixture to room temperature and, cautiously, pour the reaction mixture into dilute hydrochloric acid and ice with vigorous stirring. Separate the liquid phases and discard the benzene layer. Extract the aqueous layer with ethyl-acetate, then wash the extract with saturated sodium bicarbonate and water. Dry the extract over anhydrous sodium sulfate, filter and vaporate to a residue. Crystallize the residue from a 9:1 mixture of toluene:ethanol to obtain the title product. Dissolve 0.53 g Reflux the mixture overnight (17 hours) with vigorous stirring Separate the liquid phases Extract the aqueous layer with ethyl-acetate wash the extract with saturated sodium bicarbonate and water Dry the extract over anhydrous sodium sulfate filter Crystallize the residue from a 9:1 mixture of toluene

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

Procedure: Suspend 0.86 g. of lithium iodide in 10.0 ml. of S-collidine and add 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl] 2,2-dimethylpropionamide (see Example 5, step A). Reflux the mixture for 3 hours with vigorous stirring, then cool to room temperature. Extract the two liquid phases with ethyl acetate and water and proceed as described in Example 8 to obtain the product of this example. Reflux the mixture for 3 hours with vigorous stirring Extract the two liquid phases with ethyl acetate and water to obtain the product of this example

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

Procedure: Suspend 0.86 g. of lithium iodide in 10.0 ml. of S-collidine and add 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl] 2,2-dimethylpropionamide (see Example 5, step A). Reflux the mixture for 3 hours with vigorous stirring, then cool to room temperature. Extract the two liquid phases with ethyl acetate and water and proceed as described in Example 8 to obtain the product of this example. Reflux the mixture for 3 hours with vigorous stirring Extract the two liquid phases with ethyl acetate and water to obtain the product of this example

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

Procedure: Mix 2.2 g. of lithium iodide trihydrate and 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl]-2,2-dimethylpropionamide, as prepared in Example 5, step A, heat under nitrogen to 180° and hold for 6 hours. Allow the melt to cool to room temperature, then dissolve the solid mixture by shaking with an ethyl acetate-water mixture. Separate the layers and wash the ethyl acetate layer with 2N hydrochloric acid, water, saturated aqueous sodium thiosulfate, saturated sodium bicarbonate and water in the order set forth. Dry the ethyl acetate solution over anhydrous sodium sulfate, filter and evaporate to a residue. Crystallize the residue from a 9:1 mixture of toluene:ethanol to obtain the title product. Mix 2.2 g heat under nitrogen to 180° dissolve the solid mixture Separate the layers wash the ethyl acetate layer with 2N hydrochloric acid, water, saturated aqueous sodium thiosulfate, saturated sodium bicarbonate and water in the order Dry the ethyl acetate solution over anhydrous sodium sulfate filter evaporate to a residue Crystallize the residue from a 9:1 mixture of toluene

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

Procedure: Mix 2.2 g. of lithium iodide trihydrate and 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl]-2,2-dimethylpropionamide, as prepared in Example 5, step A, heat under nitrogen to 180° and hold for 6 hours. Allow the melt to cool to room temperature, then dissolve the solid mixture by shaking with an ethyl acetate-water mixture. Separate the layers and wash the ethyl acetate layer with 2N hydrochloric acid, water, saturated aqueous sodium thiosulfate, saturated sodium bicarbonate and water in the order set forth. Dry the ethyl acetate solution over anhydrous sodium sulfate, filter and evaporate to a residue. Crystallize the residue from a 9:1 mixture of toluene:ethanol to obtain the title product. Mix 2.2 g heat under nitrogen to 180° dissolve the solid mixture Separate the layers wash the ethyl acetate layer with 2N hydrochloric acid, water, saturated aqueous sodium thiosulfate, saturated sodium bicarbonate and water in the order Dry the ethyl acetate solution over anhydrous sodium sulfate filter evaporate to a residue Crystallize the residue from a 9:1 mixture of toluene

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

Procedure: Dissolve 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl]-2,2-dimethylpropionamide in 10 ml. of benzene and 15 g. of aluminum chloride. Reflux the mixture overnight (17 hours) with vigorous stirring. Cool the mixture to room temperature and, cautiously, pour the reaction mixture into dilute hydrochloric acid and ice with vigorous stirring. Separate the liquid phases and discard the benzene layer. Extract the aqueous layer with ethyl-acetate, then wash the extract with saturated sodium bicarbonate and water. Dry the extract over anhydrous sodium sulfate, filter and evaporate to a residue. Crystallize the residue from a 9:1 mixture of toluene:ethanol to obtain the title product. Dissolve 0.53 g Reflux the mixture overnight (17 hours) with vigorous stirring Separate the liquid phases Extract the aqueous layer with ethyl-acetate wash the extract with saturated sodium bicarbonate and water Dry the extract over anhydrous sodium sulfate filter evaporate to a residue Crystallize the residue from a 9:1 mixture of toluene

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

Procedure: Suspend 0.86 g. of lithium iodide in 10.0 ml. of S-collidine and add 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl]2,2-dimethylpropionamide (see Example 5, step A). Reflux the mixture for 3 hours with vigorous stirring, then cool to room temperature. Extract the two liquid phases with ethyl acetate and water and proceed as described in Example 8 to obtain the product of this example. Reflux the mixture for 3 hours with vigorous stirring Extract the two liquid phases with ethyl acetate and water to obtain the product of this example

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

Procedure: Mix 2.2 g. of lithium iodide trihydrate and 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl]-2,2-dimethylpropionamide, as prepared in Example 5, step A, heat under nitrogen to 180° and hold for 6 hours. Allow the melt to cool to room temperature, then dissolve the solid mixture by shaking with an ethyl acetate-water mixture. Separate the layers and wash the ethyl acetate layer with 2N hydrochloric acid, water, saturated aqueous sodium thiosulfate, saturated sodium bicarbonate and water in the order set forth. Dry the ethyl acetate solution over anhydrous sodium sulfate, filter and evaporate to a residue. Crystallize the residue from a 9:1 mixture of toluene:ethanol to obtain the title product. Mix 2.2 g heat under nitrogen to 180° dissolve the solid mixture Separate the layers wash the ethyl acetate layer with 2N hydrochloric acid, water, saturated aqueous sodium thiosulfate, saturated sodium bicarbonate and water in the order Dry the ethyl acetate solution over anhydrous sodium sulfate filter evaporate to a residue Crystallize the residue from a 9:1 mixture of toluene

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

Procedure: Dissolve 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl]-2,2-dimethylpropionamide in 10 ml. of benzene and 15 g. of aluminum chloride. Reflux the mixture overnight (17 hours) with vigorous stirring. Cool the mixture to room temperature and, cautiously, pour the reaction mixture into dilute hydrochloric acid and ice with vigorous stirring. Separate the liquid phases and discard the benzene layer. Extract the aqueous layer with ethyl-acetate, then wash the extract with saturated sodium bicarbonate and water. Dry the extract over anhydrous sodium sulfate, filter and vaporate to a residue. Crystallize the residue from a 9:1 mixture of toluene:ethanol to obtain the title product. Dissolve 0.53 g Reflux the mixture overnight (17 hours) with vigorous stirring Separate the liquid phases Extract the aqueous layer with ethyl-acetate wash the extract with saturated sodium bicarbonate and water Dry the extract over anhydrous sodium sulfate filter Crystallize the residue from a 9:1 mixture of toluene

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

Procedure: Suspend 0.86 g. of lithium iodide in 10.0 ml. of S-collidine and add 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl] 2,2-dimethylpropionamide (see Example 5, step A). Reflux the mixture for 3 hours with vigorous stirring, then cool to room temperature. Extract the two liquid phases with ethyl acetate and water and proceed as described in Example 8 to obtain the product of this example. Reflux the mixture for 3 hours with vigorous stirring Extract the two liquid phases with ethyl acetate and water to obtain the product of this example

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

Procedure: Mix 2.2 g. of lithium iodide trihydrate and 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl]-2,2-dimethylpropionamide, as prepared in Example 5, step A, heat under nitrogen to 180° and hold for 6 hours. Allow the melt to cool to room temperature, then dissolve the solid mixture by shaking with an ethyl acetate-water mixture. Separate the layers and wash the ethyl acetate layer with 2N hydrochloric acid, water, saturated aqueous sodium thiosulfate, saturated sodium bicarbonate and water in the order set forth. Dry the ethyl acetate solution over anhydrous sodium sulfate, filter and evaporate to a residue. Crystallize the residue from a 9:1 mixture of toluene:ethanol to obtain the title product. Mix 2.2 g heat under nitrogen to 180° dissolve the solid mixture Separate the layers wash the ethyl acetate layer with 2N hydrochloric acid, water, saturated aqueous sodium thiosulfate, saturated sodium bicarbonate and water in the order Dry the ethyl acetate solution over anhydrous sodium sulfate filter evaporate to a residue Crystallize the residue from a 9:1 mixture of toluene