2-(2-Bromoethoxy)anisole

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: 0.2 mole(22.4 ml) of guaiacol and 0.4 mole (34.6 ml) of ethylene dibromide are heated to 100° C. while stirring vigorously, and within 30 minutes, 125 ml of 1.6 N sodium hydroxide solution is added to continue the stirring and the pH value is adjusted to 7. Upon cooling, the mixed solution's organic layer is extracted with chloroform and rinsed with 2N sodium hydroxide before rising again with saturated sodium chloride solution and magnesium sulfate. Upon reduction, the solution is filled into the silicone tube for separation. Using the ratio of hexane: ethyl acetate=9:1 as the diluent, white crystallized product, 2-(2-methoxyphenoxy ethylbromide, is obtained. Upon cooling the mixed solution's organic layer is extracted with chloroform rinsed with 2N sodium hydroxide Upon reduction, the solution is filled into the silicone tube for separation

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

Procedure: 0.2 mole(22.4 ml) of guaiacol and 0.4 mole (34.6 ml) of ethylene dibromide are heated to 100° C. while stirring vigorously, and within 30 minutes, 125 ml of 1.6 N sodium hydroxide solution is added to continue the stirring and the pH value is adjusted to 7. Upon cooling, the mixed solution's organic layer is extracted with chloroform and rinsed with 2N sodium hydroxide before rising again with saturated sodium chloride solution and magnesium sulfate. Upon reduction, the solution is filled into the silicone tube for separation. Using the ratio of hexane: ethyl acetate=9:1 as the diluent, white crystallized product, 2-(2-methoxyphenoxy ethylbromide, is obtained. Upon cooling the mixed solution's organic layer is extracted with chloroform rinsed with 2N sodium hydroxide Upon reduction, the solution is filled into the silicone tube for separation

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

Procedure: A mixture of 2-bromoethyl 2-methoxyphenyl ether (7.5 g), 4-(2-dimethylaminoethyl)piperidine dihydrochloride (7.44 g), triethylamine (18.1 ml) and DMF (50 ml) was heated on a steam bath for 18 hours. The mixture was poured into ice/water (500 ml) and basified with 2M sodium hydroxide. The product was extracted into dichloromethane to give an oil. The oil was triturated with ether. The ether was decanted off and evaporated to give crude 4-(2-dimethylaminoethyl)-1-[2-(2-methoxyphenoxy)ethyl]piperidine (4.58 g) which was added to glacial acetic acid (17 ml) and 48% hydrobromic acid (57 ml). The mixture was heated on a steam bath for 4 hours and then evaporated to dryness. The residue was dissolved in water, basified with 2M sodium hydroxide solution and extracted with dichloromethane to give an oil. The oil was dissolved in ether and acidified with ethereal hydrogen chloride The precipitate was collected by filtration and recrystallised from propan-2-ol to give 2-{2-[4-(2-dimethylaminoethyl)piperidino]ethoxy}phenol dihydrochloride m.p. 273°-275° C. was heated on a steam bath for 18 hours The product was extracted into dichloromethane to give an oil The oil was triturated with ether The ether was decanted off evaporated to give crude 4-(2-dimethylaminoethyl)-1-[2-(2-methoxyphenoxy)ethyl]piperidine (4.58 g) which The mixture was heated on a steam bath for 4 hours evaporated to dryness The residue was dissolved in water extracted with dichloromethane to give an oil was collected by filtration recrystallised from propan-2-ol

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

Procedure: 2-(2-Methoxyphenoxy)ethyl bromide (2.31 g.), 4-benzamidopiperidine (2.04 g.) and anhydrous potassium carbonate (1.38 g.) were well mixed and heated on a steam bath for 4 hr. The resultng mass was crushed and stirred in water (200 ml.) at 60° for 12 hr. Filtration afforded the crude base of the title compound (2.95 g.). Conversion to the hydrochloride by solution in ethanol/HCl and precipitation with ether provided 3.01 g. of the title compound, as the hydrochloride m.p. 193.4° . heated on a steam bath for 4 hr The resultng mass was crushed Filtration

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

Procedure: 2-(2-Methoxyphenoxy)ethyl bromide (2.31 g.), 4-benzamidopiperidine (2.04 g.) and anhydrous potassium carbonate (1.38 g.) were well mixed and heated on a steam bath for 4 hr. The resultng mass was crushed and stirred in water (200 ml.) at 60° for 12 hr. Filtration afforded the crude base of the title compound (2.95 g.). Conversion to the hydrochloride by solution in ethanol/HCl and precipitation with ether provided 3.01 g. of the title compound, as the hydrochloride m.p. 193.4° . heated on a steam bath for 4 hr The resultng mass was crushed Filtration

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: A solution of 1-(2-bromoethoxy)-2-methoxybenzene (7d) (7.7 g, 33 mmol) in a 33% solution of methylamine in ethanol was heated at 80° C. in a sealed tube for 16 h. After cooling to room temperature, the solvents were evaporated in vacuo. A 2N aqueous solution of sodium hydroxide was added to the remaining oil and the resulting slurry was extracted with ethyl acetate (2×250 mL). The collected organic phases were dried (Na2SO4) and the solvents evaporated in vacuo giving 5.9 g (98%) of the title compound as an oil: 1H NMR (CDCl3) δ 1.85 (broad s, 1H), 2.50 (s, 3H), 3.00 (t, 2H), 3.85 (s, 3H), 4.10 (t, 2H), 6.85-6.95 (m, 4H). the solvents were evaporated in vacuo A 2N aqueous solution of sodium hydroxide was added to the remaining oil the resulting slurry was extracted with ethyl acetate (2×250 mL) The collected organic phases were dried (Na2SO4) the solvents evaporated in vacuo

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

Procedure: A solution of 1-(2-bromoethoxy)-2-methoxybenzene (7d) (7.7 g, 33 mmol) in a 33% solution of methylamine in ethanol was heated at 80° C. in a sealed tube for 16 h. After cooling to room temperature, the solvents were evaporated in vacuo. A 2N aqueous solution of sodium hydroxide was added to the remaining oil and the resulting slurry was extracted with ethyl acetate (2×250 mL). The collected organic phases were dried (Na2SO4) and the solvents evaporated in vacuo giving 5.9 g (98%) of the title compound as an oil: 1H NMR (CDCl3) δ 1.85 (broad s, 1H), 2.50 (s, 3H), 3.00 (t, 2H), 3.85 (s, 3H), 4.10 (t, 2H), 6.85-6.95 (m, 4H). the solvents were evaporated in vacuo A 2N aqueous solution of sodium hydroxide was added to the remaining oil the resulting slurry was extracted with ethyl acetate (2×250 mL) The collected organic phases were dried (Na2SO4) the solvents evaporated in vacuo

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

Procedure: 2-(2-Methoxyphenoxy)ethyl bromide (2.31 g.), 4-benzamidopiperidine (2.04 g.) and anhydrous potassium carbonate (1.38 g.) were well mixed and heatedon a steam bath for 4 hr. The resulting mass was crushed and stirred in water (200 ml.) at 60° for 12 hr. Filtration afforded the crude base of the title compound (2.95 g.). Conversion to the hydrochloride by solution in ethanol/HCl and precipitation with ether provided 3.01 g. of the title compound, as the hydrochloride m.p. 193.4°. Analysis : Found C, 64.74; H, 7.08; N, 7.14. C21H26N2O3. HCl requires C, 64.52; H, 6.96; N, 7.17%. The resulting mass was crushed Filtration