2-(chloromethyl)-1,3-dimethoxybenzene

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: To a stirred solution of 6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (2.7 g. 0.01 mole) in 30 ml. of dry dimethyl formamide was added sodium hydride (0.5 g., 0.02 mole of 50% dispersion in mineral oil). When the evolution of hydrogen subsides, 2.7 g. (0.01 mole) of 2,6-dimethoxybenzyl chloride was added. The reaction mixture was stirred at room temperature for eighteen hours, and the dimethyl formamide was removed under vacuo. The residue was triturated with cold water, filtered and recrystallized from ethanol to give white crystals of the title compound, 2.7 g. (89% yield) m.p. 200°-202° C.; hydrochloride salt, m.p. 220°-223° C. the dimethyl formamide was removed under vacuo The residue was triturated with cold water filtered recrystallized from ethanol

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

Procedure: To a stirred solution of 6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (2.7 g. 0.01 mole) in 30 ml. of dry dimethyl formamide was added sodium hydride (0.5 g., 0.02 mole of 50% dispersion in mineral oil). When the evolution of hydrogen subsides, 2.7 g. (0.01 mole) of 2,6-dimethoxybenzyl chloride was added. The reaction mixture was stirred at room temperature for eighteen hours, and the dimethyl formamide was removed under vacuo. The residue was triturated with cold water, filtered and recrystallized from ethanol to give white crystals of the title compound, 2.7 g. (89% yield) m.p. 200°-202° C.; hydrochloride salt, m.p. 220°-223° C. the dimethyl formamide was removed under vacuo The residue was triturated with cold water filtered recrystallized from ethanol

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: On the other hand, 1.66 g (9.0 mmol) of 1-(4-chloro-6-methyl-2-pyridinyl)ethanone oxime was dissolved in 15 ml of N,N-dimethylformamide, and the resultant solution was added with 0.18 g (4.39 mmol) of sodium hydride (60%, oiliness) while cooling the solution with ice. The mixture was stirred for 15 min. at a temperature below 0° C. and was added with the whole amount of the crude product of 2,6-dimethoxybenzyl chloride prepared previously while cooling the mixture with ice. The resultant mixture was stirred for 2.3 hours at a room temperature to complete a reaction. The reacted mixture was then poured into ice water. At that time, the target compound was precipitated in the ice water. The precipitation was taken out by filtering, washed with hexane and dried to thereby obtain the target compound in an amount of 2.3 g. while cooling the solution with ice prepared previously while cooling the mixture with ice a reaction At that time, the target compound was precipitated in the ice water The precipitation by filtering washed with hexane dried to thereby obtain the target compound in an amount of 2.3 g

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

Procedure: 1.86 g (11.1 mmol) of 2,6-dimethoxybenzyl alcohol was dissolved in 15 ml of benzene, and the resultant solution was cooled to 5° C. The solution was then added with 1.55 g (13.0mmol) of thionyl chloride at the same temperature. The mixture was subjected to temperature elevation up to a room temperature, then stirred for 70 min. to complete a reaction. The reacted solution was condensed under reduced pressure to thereby obtain a crude product of 2,6-dimethoxybenzyl chloride. was subjected to temperature elevation up to a room temperature a reaction condensed under reduced pressure

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

Procedure: 0.49 g (2.93 mmol) of 2,6-dimethoxybenzyl alcohol was dissolved in 6 ml of benzene, and the resultant solution was added with 0.41 g (3.32 mmol) of thionyl chloride at a room temperature. The thus obtained solution was then stirred for 1.5 hours at a room temperature to complete a reaction. The reacted solution was then condensed under reduced pressure to obtain a crude product of 2,6-dimethoxybenzyl chloride. a reaction condensed under reduced pressure

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

Procedure: 0.43 g (2.56 mmol) of 2,6-dimethoxybenzyl alcohol was dissolved in 5 ml of benzene, and the resultant solution was added with 0.40 g (3.36 mmol) of thionyl chloride at a room temperature. The mixture was then stirred for an hour at a room temperature to facilitate the provided compounds to react. The reacted solution was then condensed under reduced pressure to obtain a crude product of 2,6-dimethoxybenzyl chloride. to react condensed under reduced pressure

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

Procedure: To a stirred solution of 6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (2.7 g. 0.01 mole) in 30 ml. of dry dimethyl formamide was added sodium hydride (0.5 g., 0.02 mole of 50% dispersion in mineral oil). When the evolution of hydrogen subsides, 2.7 g. (0.01 mole) of 2,6-dimethoxybenzyl chloride was added. The reaction mixture was stirred at room temperature for eighteen hours, and the dimethyl formamide was removed under vacuo. The residue was triturated with cold water, filtered and recrystallized from ethanol to give white crystals of the title compound, 2.7 g. (89% yield) m.p. 200°-202° C.; hydrochloride salt, m.p. 220°-223° C. the dimethyl formamide was removed under vacuo The residue was triturated with cold water filtered recrystallized from ethanol