N,N-diethyl-2-methoxyethanamine

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: Next, 8.24 g of the 2-methoxyethyldiethylamine was dissolved in 10 mL of tetrahydrofuran (Wako Pure Chemical Industries), then 4.0 mL of methyl iodide (Wako Pure Chemical Industries) was added under ice cooling. After 30 minutes, the mixture was removed from the ice bath and stirred overnight at room temperature. The solvent in this reaction solution was subsequently driven off by vacuum distillation, and the resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran system, yielding 16 g of 2-methoxyethyldiethylmethylammonium iodide. the mixture was removed from the ice bath The solvent in this reaction solution was subsequently driven off by vacuum distillation the resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran system

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

Procedure: Next, 8.24 g of the 2-methoxyethyldiethylamine was dissolved in 10 mL of tetrahydrofuran (Wako Pure Chemical Industries), then 4.0 mL of methyl iodide (Wako Pure Chemical Industries) was added under ice cooling. After 30 minutes, the mixture was removed from the ice bath and stirred overnight at room temperature. The solvent in this reaction solution was subsequently driven off by vacuum distillation, and the resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran system, yielding 16 g of 2-methoxyethyldiethylmethylammonium iodide. the mixture was removed from the ice bath The solvent in this reaction solution was subsequently driven off by vacuum distillation the resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran system

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: Next, 8.24 g of the 2-methoxyethyldiethylamine was dissolved in 10 ml of tetrahydrofuran (Wako Pure Chemical Industries), following which 4.0 ml of methyl iodide (Wako Pure Chemical Industries) was added under ice cooling. After 30 minutes, the mixture was removed from the ice bath and stirred overnight at room temperature. The solvent in the resulting reaction mixture was then driven off by vacuum distillation, and the resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran system, yielding 16 g of 2-methoxyethyldiethylmethylammonium iodide. was added under ice cooling the mixture was removed from the ice bath The solvent in the resulting reaction mixture was then driven off by vacuum distillation the resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran system

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

Procedure: Next, 8.24 g of the 2-methoxyethyldiethylamine was dissolved in 10 ml of tetrahydrofuran (Wako Pure Chemical Industries), following which 4.0 ml of methyl iodide (Wako Pure Chemical Industries) was added under ice cooling. After 30 minutes, the mixture was removed from the ice bath and stirred overnight at room temperature. The solvent in the resulting reaction mixture was then driven off by vacuum distillation, and the resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran system, yielding 16 g of 2-methoxyethyldiethylmethylammonium iodide. was added under ice cooling the mixture was removed from the ice bath The solvent in the resulting reaction mixture was then driven off by vacuum distillation the resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran system

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

Procedure: In an autoclave of 100 mL, N,N-diethylamine (35.0 g, 478 mmol) was made reacted with chloroethyl methyl ether (22.6 g, 239 mmol) at 120 deg C. for 48 hours. Solid salt that was formed was removed by filtration, and residue (filtrate) was subjected to reduced-pressure distillation by using a Vigreux column of 25 cm. Then 1H-NMR measurement of obtained amine is performed, and it was confirmed that chemical shifts, δ (ppm), are 3.45-3.42 (t, 2H), 3.31(s, 3H), 2.52-2.50(t, 2H), 2.34-2.31(t, 2H), 2.22(s, 3H), 1.45-1.38(m, 2H), 1.31-1.22(m, 2H), and 0.89-0.85(t, 3H), and that N,N-diethyl-N-2-methoxyethylamine was synthesized. Solid salt that was formed was removed by filtration, and residue (filtrate) was subjected to reduced-pressure distillation

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

Procedure: In an autoclave of 100 mL, N,N-diethylamine (35.0 g, 478 mmol) was made reacted with chloroethyl methyl ether (22.6 g, 239 mmol) at 120 deg C. for 48 hours. Solid salt that was formed was removed by filtration, and residue (filtrate) was subjected to reduced-pressure distillation by using a Vigreux column of 25 cm. Then 1H-NMR measurement of obtained amine is performed, and it was confirmed that chemical shifts, δ (ppm), are 3.45-3.42 (t, 2H), 3.31(s, 3H), 2.52-2.50(t, 2H), 2.34-2.31(t, 2H), 2.22(s, 3H), 1.45-1.38(m, 2H), 1.31-1.22(m, 2H), and 0.89-0.85(t, 3H), and that N,N-diethyl-N-2-methoxyethylamine was synthesized. Solid salt that was formed was removed by filtration, and residue (filtrate) was subjected to reduced-pressure distillation

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

Procedure: Next, 41.2 g of the 2-methoxyethyldiethylamine was dissolved in 300 mL of tetrahydrofuran (Wako Pure Chemical Industries, Inc.), following which 20.0 mL of methyl iodide (Wako Pure Chemical Industries) was added under ice cooling. After 30 minutes, the ice bath was removed and stirring was carried out overnight at room temperature. The solvent in this reaction solution was driven off by vacuum distillation, and the resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran mixture, yielding 80 g of 2-methoxyethyldiethylmethylammonium iodide. was added under ice cooling the ice bath was removed was carried out overnight at room temperature The solvent in this reaction solution was driven off by vacuum distillation the resulting solids were recrystallized from an ethanol (Wako Pure Chemical Industries)—tetrahydrofuran mixture

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

Procedure: A mixed solution prepared by mixing 200 mL of diethylamine (Kanto Chemical Co., Ltd.) and 85 mL of 2-methoxyethyl chloride (produced by Kanto Chemical) was placed in an autoclave and reacted at 120° C. for 50 hours. The internal pressure at this time was 353 kPa (3.6 kgf/cm2). After 10 hours, the crystals that settled out were removed by filtration, and the filtrate was subjected to normal-pressure distillation, yielding 66 g of 2-methoxyethyldiethylamine. A mixed solution prepared reacted at 120° C. for 50 hours the crystals that settled out were removed by filtration the filtrate was subjected to normal-pressure distillation