2-(4-hydroxyphenoxy)-N-methylacetamide

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

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

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: In analogy to the procedure described in Example 3b), the alkylation of 2-(4-hydroxy-phenoxy)-N-methyl-acetamide [Example 3a)] with 1-bromomethyl-3-fluoro-benzene in 2-butanone using potassium carbonate as the base yielded the 2-[4-(3-fluoro-benzyloxy)-phenoxy]-N-methyl-acetamide as white crystals; MS: m/e=290 (M+H)+.

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

Procedure: In analogy to the procedure described in Example 3b), the alkylation of 2-(4-hydroxy-phenoxy)-N-methyl-acetamide [Example 3a)] with 1-bromomethyl-2-fluoro-benzene in 2-butanone using potassium carbonate as the base yielded the 2-[4-(2-fluoro-benzyloxy)-phenoxy]-N-methyl-acetamide as white crystals; MS: m/e=290 (M+H)+.

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

Procedure: In analogy to the procedure described in Example 3 b), the alkylation of 2-(4-hydroxy-phenoxy)-N-methyl-acetamide [Example 3a)] with 1-bromomethyl-4-chloro-benzene in 2-butanone using potassium carbonate as the base yielded the 2-[4-(4-chloro-benzyloxy)-phenoxy]-N-methyl-acetamide as white crystals; MS: m/e=306 (M+H)+.

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

Procedure: A solution of 500 mg of 2-(4-hydroxy-phenoxy)-N-methyl-acetamide in 25 ml of 2-butanone was treated with 762 mg of potassium carbonate and 595 mg of 4-bromomethyl-benzonitrile. The reaction mixture was stirred at room temperature for 60 h. For the working-up, the reaction mixture was treated with water, then extracted with ethyl acetate. The aqueous layer was re-extracted with ethyl acetate, the combined organic layers were dried over magnesium sulphate and evaporated under reduced pressure. The residue was triturated in ether and the crystals obtained were collected on a filter funnel. After drying there were obtained 744 mg (95% of theory) of 2-[4-(4-cyano-benzyloxy)-phenoxy]-N-methyl-acetamide as white crystals; MS: m/e=297 (M+H)+. extracted with ethyl acetate The aqueous layer was re-extracted with ethyl acetate the combined organic layers were dried over magnesium sulphate evaporated under reduced pressure The residue was triturated in ether the crystals obtained were collected on a filter funnel After drying there

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

Procedure: A solution of 4.7 g of 2-(4-benzyloxy-phenoxy)-N-methyl-acetamide [Example 2c)] in 150 ml of tetrahydrofurane was hydrogenated at atmospheric pressure and room temperature using 470 mg of palladium on charcoal (10%) as the catalyst. For the working-up, the reaction mixture was filtered over a Dicalite layer and the resulting solution was evaporated under reduced pressure. The residue was triturated in ether and the solid collected on a filter funnel. After drying there were obtained 2.95 g (93% of theory) of 2-(4-hydroxy-phenoxy)-N-methyl-acetamide as white crystals; MS: m/e=181 (M)+. was hydrogenated at atmospheric pressure and room temperature the reaction mixture was filtered over a Dicalite layer the resulting solution was evaporated under reduced pressure The residue was triturated in ether the solid collected on a filter funnel After drying there

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: In analogy to the procedure described in Example 3b), the alkylation of 2-(4-hydroxy-phenoxy)-N-methyl-acetamide [Example 3a)] with 1-bromomethyl-3-fluoro-benzene in 2-butanone using potassium carbonate as the base yielded the 2-[4-(3-fluoro-benzyloxy)-phenoxy]-N-methyl-acetamide as white crystals; MS: m/e=290 (M+H)+.