6-bromohexoxybenzene

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: 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride as starting compound and 6-phenoxyhexyl bromide (1.56 g) were reacted and treated in the same manner as in Example 168 to give 0.78 g of 4-amino-5-chloro-2-methoxy-N-((1-(6-phenoxyhexyl)piperidin-4-yl)methyl)benzamide. were reacted treated in the same manner as in Example 168

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

Procedure: 60% Sodium hydride (1.16 g) was suspended in dimethylformamide (40 ml), and phenol (3 g) was added under ice-cooilng with stirring. The mixture was stirred at room temperature for 1 hr. The mixture was again ice-cooled, and a solution of 1,6-dibromohexane (7.78 g) in dimethylformamide (10 ml) was dropwise added, which was followed by stirring at room temperature for 2 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure to give 8.2 g of 6-phenoxyhexyl bromide. The mixture was stirred at room temperature for 1 hr cooled by stirring at room temperature for 2 hr the mixture was extracted with ethyl acetate The organic layer was washed with brine dried the solvent was evaporated under reduced pressure

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

Procedure: 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride as starting compound and 6-phenoxyhexyl bromide (1.56 g) were reacted and treated in the same manner as in Example 168 to give 0.78 g of 4-amino-5-chloro-2-methoxy-N-((1-(6-phenoxyhexyl)piperidin-4-yl)methyl)benzamide. were reacted treated in the same manner as in Example 168

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

Procedure: 60% Sodium hydride (1.16 g) was suspended in dimethylformamide (40 ml), and phenol (3 g) was added under ice-cooilng with stirring. The mixture was stirred at room temperature for 1 hr. The mixture was again ice-cooled, and a solution of 1,6-dibromohexane (7.78 g) in dimethylformamide (10 ml) was dropwise added, which was followed by stirring at room temperature for 2 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure to give 8.2 g of 6-phenoxyhexyl bromide. The mixture was stirred at room temperature for 1 hr cooled by stirring at room temperature for 2 hr the mixture was extracted with ethyl acetate The organic layer was washed with brine dried the solvent was evaporated under reduced pressure

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

Procedure: 60% Sodium hydride (1.16 g) was suspended in dimethylformamide (40 ml), and phenol (3 g) was added under ice-cooilng with stirring. The mixture was stirred at room temperature for 1 hr. The mixture was again ice-cooled, and a solution of 1,6-dibromohexane (7.78 g) in dimethylformamide (10 ml) was dropwise added, which was followed by stirring at room temperature for 2 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure to give 8.2 g of 6-phenoxyhexyl bromide. The mixture was stirred at room temperature for 1 hr cooled by stirring at room temperature for 2 hr the mixture was extracted with ethyl acetate The organic layer was washed with brine dried the solvent was evaporated under reduced pressure

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

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.724 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.175 g), stirred for 15 minutes and treated with (6-bromohexyloxy)benzene (1.5 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material from dichloromethane extraction was purified by HPLC (dichloromethane-hexane; 5:1) and crystallized from diethyl ether-hexane to provide 0.95 g of alpha-oxo-4-[[(6-phenoxy)hexyl]oxy]benzeneacetic acid methyl ester, mp 50°-52° C. The material from dichloromethane extraction was purified by HPLC (dichloromethane-hexane; 5:1) crystallized from diethyl ether-hexane

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.724 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.175 g), stirred for 15 minutes and treated with (6-bromohexyloxy)benzene (1.5 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material from dichloromethane extraction was purified by HPLC (dichloromethane-hexane; 5:1) and crystallized from diethyl ether-hexane to provide 0.95 g of alpha-oxo-4-[[(6-phenoxy)hexyl]oxy]benzeneacetic acid methyl ester, mp 50°-52° C. The material from dichloromethane extraction was purified by HPLC (dichloromethane-hexane; 5:1) crystallized from diethyl ether-hexane

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

Procedure: Preparation analogously to Example 38 by the reaction of sodium phenolate with 1,6-dibromohexane to give 6-phenoxy-1-bromohexane (b.p.11 =172°-5°; yield 77%), which is reacted with excess 5-amino-5-desoxy-1.4;3.6-dianhydro-L-iditol 2-nitrate. Isolation as hydrochloride. Yield, after recrystallisation from isopropanol: 53%. Preparation analogously to Example 38