N-[2-(4-hydroxyphenyl)ethyl]acetamide

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

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

Procedure: Potassium carbonate (3.5 g, 25.5 mol) and iodomethane(2.0 ml, 31.9 mmol) was added to a solution of N-(4-hydroxyphenylethyl)acetamide (4.4 g, 24.6 mmol) in ethanol(2.4 ml), which was then refluxed for 12 hours. The resulting solid was filtered and washed with ethanol. The filtrate was concentrated to give oily residue, which was diluted with ethyl acetate and washed with water. The separated organic layer was concentrated and the resulting solid was suspended in ethylether, filtered, and dried to give 2.9 g of the titled compound. was then refluxed for 12 hours The resulting solid was filtered washed with ethanol The filtrate was concentrated to give oily residue, which washed with water The separated organic layer was concentrated filtered dried

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

Procedure: Potassium carbonate (3.5 g, 25.5 mol) and iodomethane(2.0 ml, 31.9 mmol) was added to a solution of N-(4-hydroxyphenylethyl)acetamide (4.4 g, 24.6 mmol) in ethanol(2.4 ml), which was then refluxed for 12 hours. The resulting solid was filtered and washed with ethanol. The filtrate was concentrated to give oily residue, which was diluted with ethyl acetate and washed with water. The separated organic layer was concentrated and the resulting solid was suspended in ethylether, filtered, and dried to give 2.9 g of the titled compound. was then refluxed for 12 hours The resulting solid was filtered washed with ethanol The filtrate was concentrated to give oily residue, which washed with water The separated organic layer was concentrated filtered dried

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

Procedure: A solution of sodium hydroxide(2.3 g, 58 mmol) in water(20 ml) was cooled to 0° C. A solution of N-(4-acetoxyphenylethyl)acetamide(6.4 g, 29 mmol) in methanol(40 ml) was added dropwise to the soultion, stirred for 10 minutes, adjusted to pH 1 with hydrochloric acid, and then extracted 3 times with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated. The resulting oily residue was solidified with ethyl ether, filtered, and dried to give 4.4 g of the titled compound. extracted 3 times with ethyl acetate The extract was washed with water dried over anhydrous magnesium sulfate concentrated filtered dried

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

Procedure: A solution of sodium hydroxide(2.3 g, 58 mmol) in water(20 ml) was cooled to 0° C. A solution of N-(4-acetoxyphenylethyl)acetamide(6.4 g, 29 mmol) in methanol(40 ml) was added dropwise to the soultion, stirred for 10 minutes, adjusted to pH 1 with hydrochloric acid, and then extracted 3 times with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated. The resulting oily residue was solidified with ethyl ether, filtered, and dried to give 4.4 g of the titled compound. extracted 3 times with ethyl acetate The extract was washed with water dried over anhydrous magnesium sulfate concentrated filtered dried

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

Procedure: Potassium carbonate (3.5 g, 25.5 mol) and iodomethane(2.0 ml, 31.9 mmol) was added to a solution of N-(4-hydroxyphenylethyl)acetamide (4.4 g, 24.6 mmol) in ethanol(2.4 ml), which was then refluxed for 12 hours. The resulting solid was filtered and washed with ethanol. The filtrate was concentrated to give oily residue, which was diluted with ethyl acetate and washed with water. The separated organic layer was concentrated and the resulting solid was suspended in ethylether, filtered, and dried to give 2.9 g of the titled compound. was then refluxed for 12 hours The resulting solid was filtered washed with ethanol The filtrate was concentrated to give oily residue, which washed with water The separated organic layer was concentrated filtered dried

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

Procedure: A solution of sodium hydroxide(2.3 g, 58 mmol) in water(20 ml) was cooled to 0° C. A solution of N-(4-acetoxyphenylethyl)acetamide(6.4 g, 29 mmol) in methanol(40 ml) was added dropwise to the soultion, stirred for 10 minutes, adjusted to pH 1 with hydrochloric acid, and then extracted 3 times with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated. The resulting oily residue was solidified with ethyl ether, filtered, and dried to give 4.4 g of the titled compound. extracted 3 times with ethyl acetate The extract was washed with water dried over anhydrous magnesium sulfate concentrated filtered dried

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

Procedure: A mixture of 17.92 g. (0.1 mol) 4-(2-acetamino-ethyl)-phenol, 17.3 g. (0.125 mol) pulverized potassium carbonate and 150 ml. butan-2-one is stirred for 2 hours at reflux temperature, then 27.9 g. (0.125 mol) ethyl 2-bromohexanoate and a spatula tip of potassium iodide are added thereto and the reaction mixture kept at reflux temperature for a further 28 hours. The reaction mixture is then filtered with suction and the filtrate evaporated in a vacuum. The residue is taken up in diethyl ether and the ethereal phase is extracted with 2 N hydrochloric acid, water, 0.5 N aqueous sodium hydroxide solution and again with water, dried over anhydrous sodium sulphate and evaporated to give 32.1 g. (quantitative yield) ethyl 2-[4-(2-acetaminoethyl)-phenoxy]-n-hexanoate in the form of a colorless oil with a refractive index nD20 =1.5010. A mixture of 17.92 g at reflux temperature at reflux temperature for a further 28 hours The reaction mixture is then filtered with suction the filtrate evaporated in a vacuum the ethereal phase is extracted with 2 N hydrochloric acid, water, 0.5 N aqueous sodium hydroxide solution and again with water dried over anhydrous sodium sulphate evaporated to give 32.1 g

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

Procedure: A mixture of 17.92 g. (0.1 mol) 4-(2-acetamino-ethyl)-phenol, 17.3 g. (0.125 mol) pulverized potassium carbonate and 150 ml. butan-2-one is stirred for 2 hours at reflux temperature, then 27.9 g. (0.125 mol) ethyl 2-bromohexanoate and a spatula tip of potassium iodide are added thereto and the reaction mixture kept at reflux temperature for a further 28 hours. The reaction mixture is then filtered with suction and the filtrate evaporated in a vacuum. The residue is taken up in diethyl ether and the ethereal phase is extracted with 2 N hydrochloric acid, water, 0.5 N aqueous sodium hydroxide solution and again with water, dried over anhydrous sodium sulphate and evaporated to give 32.1 g. (quantitative yield) ethyl 2-[4-(2-acetaminoethyl)-phenoxy]-n-hexanoate in the form of a colorless oil with a refractive index nD20 =1.5010. A mixture of 17.92 g at reflux temperature at reflux temperature for a further 28 hours The reaction mixture is then filtered with suction the filtrate evaporated in a vacuum the ethereal phase is extracted with 2 N hydrochloric acid, water, 0.5 N aqueous sodium hydroxide solution and again with water dried over anhydrous sodium sulphate evaporated to give 32.1 g

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

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

Procedure: N-[2-(4-Hydroxyphenyl)ethyl]acetamide (668.3 mg, 3.73 mmol), 2-chloro-5-cyclopentyloxypyridine (737 mg, 3.73 mmol) and cesium carbonate (1.458 g, 4.475 mmol) were treated at 230° C. in 24 ml of DMF in a microwave reactor for 2 h. The reaction mixture was concentrated, and the residue was taken up in ethyl acetate and water. The organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 8 mg (1%), M+H+: 341.13. The reaction mixture was concentrated The organic phase was separated off concentrated purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

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

Procedure: Potassium carbonate (3.5 g, 25.5 mol) and iodomethane(2.0 ml, 31.9 mmol) was added to a solution of N-(4-hydroxyphenylethyl)acetamide (4.4 g, 24.6 mmol) in ethanol(2.4 ml), which was then refluxed for 12 hours. The resulting solid was filtered and washed with ethanol. The filtrate was concentrated to give oily residue, which was diluted with ethyl acetate and washed with water. The separated organic layer was concentrated and the resulting solid was suspended in ethylether, filtered, and dried to give 2.9 g of the titled compound. was then refluxed for 12 hours The resulting solid was filtered washed with ethanol The filtrate was concentrated to give oily residue, which washed with water The separated organic layer was concentrated filtered dried