2-(2-bromoethoxy)-1,3-dimethylbenzene

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

Procedure: 2,6 Dimethylphenol (2 mmol) was reacted with 1,2-dibromoethane (10 eq) as described in Step 2A to yield the titled compound.

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

Procedure: To methylethylketone (1 liter) are added 2-(2,6-dimethylphenoxy)-1-bromo-ethane (132 g), sodium iodide (85 g), potassium carbonate (80 g) and piperazine (200 g). The mixture is refluxed for 24 hours, with stirring. After cooling, the mixture is filtered and then washed with 3×300 ml benzene. After evaporation of the benzene, the piperazine derivative is distilled; b.p. 25 mm Hg=190° C. The mixture is refluxed for 24 hours After cooling the mixture is filtered washed with 3×300 ml benzene After evaporation of the benzene the piperazine derivative is distilled b.p. 25 mm Hg=190° C.

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

Procedure: To a solution containing sodium hydroxide (80 g) in water (1 liter) and ethanol (0.5 liter) are added 2,6-dimethyl-phenol (245 g) dissolved in ethanol (0.5 liter), and then dibromoethane (750 g). The mixture is refluxed for 48 hours, under vigorous stirring. It is then extracted with methylene chloride. After washing with dilute aqueous sodium hydroxide and then with water, the solvent is evaporated in vacuo. 2(2,6-Dimethyl-phenoxy)-1-bromo-ethane boils at 148°-150° C./25 mm Hg. The mixture is refluxed for 48 hours, under vigorous stirring It is then extracted with methylene chloride After washing with dilute aqueous sodium hydroxide with water, the solvent is evaporated in vacuo

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

Procedure: To methylethylketone (1 liter) are added 2-(2,6-dimethylphenoxy)-1-bromo-ethane (132 g), sodium iodide (85 g), potassium carbonate (80 g) and piperazine (200 g). The mixture is refluxed for 24 hours, with stirring. After cooling, the mixture is filtered and then washed with 3×300 ml benzene. After evaporation of the benzene, the piperazine derivative is distilled; b.p. 25 mm Hg=190° C. The mixture is refluxed for 24 hours After cooling the mixture is filtered washed with 3×300 ml benzene After evaporation of the benzene the piperazine derivative is distilled b.p. 25 mm Hg=190° C.

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

Procedure: To a solution containing sodium hydroxide (80 g) in water (1 liter) and ethanol (0.5 liter) are added 2,6-dimethyl-phenol (245 g) dissolved in ethanol (0.5 liter), and then dibromoethane (750 g). The mixture is refluxed for 48 hours, under vigorous stirring. It is then extracted with methylene chloride. After washing with dilute aqueous sodium hydroxide and then with water, the solvent is evaporated in vacuo. 2(2,6-Dimethyl-phenoxy)-1-bromo-ethane boils at 148°-150° C./25 mm Hg. The mixture is refluxed for 48 hours, under vigorous stirring It is then extracted with methylene chloride After washing with dilute aqueous sodium hydroxide with water, the solvent is evaporated in vacuo

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

Procedure: Using the procedure described in Example I and starting from 12.7 g (2,6-dimethylphenoxyethyl) bromide and 12.8 g 4-(N'-phenyl-N'-propionylamino)-piperidine, 16.1 g of the title product are obtained melting at 82° after recrystallization from hexane. Mixing the compound with 4-(N'-phenyl-N'-propionylamino)-piperidine depresses the melting point.

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

Procedure: Using the procedure described in Example I and starting from 12.7 g (2,6-dimethylphenoxyethyl) bromide and 12.8 g 4-(N'-phenyl-N'-propionylamino)-piperidine, 16.1 g of the title product are obtained melting at 82° after recrystallization from hexane. Mixing the compound with 4-(N'-phenyl-N'-propionylamino)-piperidine depresses the melting point.

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

Procedure: In 30 mm of N,N-dimethylformamide was dissolved 2.2 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 2.3 g of 2-(2',6'-dimethylphenoxy)ethyl bromide, and thereto were added 1.1 g of anhydrous sodium carbonate. The resulting solution was stirred at room temperature for fifteen hours. This solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and freed of solvent under reduced pressure to give crystals. The crystals thus obtained were washed with n-hexane to give 3.5 g of the intended compound. m.p. 104.3°~105.2° C. extracted with diethyl ether The organic layer was dried over anhydrous sodium sulfate to give crystals The crystals thus obtained were washed with n-hexane

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

Procedure: 2,6 Dimethylphenol (2 mmol) was reacted with 1,2-dibromoethane (10 eq) as described in Step 2A to yield the titled compound.

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

Procedure: To methylethylketone (1 liter) are added 2-(2,6-dimethylphenoxy)-1-bromo-ethane (132 g), sodium iodide (85 g), potassium carbonate (80 g) and piperazine (200 g). The mixture is refluxed for 24 hours, with stirring. After cooling, the mixture is filtered and then washed with 3×300 ml benzene. After evaporation of the benzene, the piperazine derivative is distilled; b.p. 25 mm Hg=190° C. The mixture is refluxed for 24 hours After cooling the mixture is filtered washed with 3×300 ml benzene After evaporation of the benzene the piperazine derivative is distilled b.p. 25 mm Hg=190° C.

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

Procedure: To a solution containing sodium hydroxide (80 g) in water (1 liter) and ethanol (0.5 liter) are added 2,6-dimethyl-phenol (245 g) dissolved in ethanol (0.5 liter), and then dibromoethane (750 g). The mixture is refluxed for 48 hours, under vigorous stirring. It is then extracted with methylene chloride. After washing with dilute aqueous sodium hydroxide and then with water, the solvent is evaporated in vacuo. 2(2,6-Dimethyl-phenoxy)-1-bromo-ethane boils at 148°-150° C./25 mm Hg. The mixture is refluxed for 48 hours, under vigorous stirring It is then extracted with methylene chloride After washing with dilute aqueous sodium hydroxide with water, the solvent is evaporated in vacuo