2-(2-methoxyphenoxy)ethanamine

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

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

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

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

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

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

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture comprising 2-(2-methoxyphenoxy)ethylamine (10 g, 59.9 mmol), diisopropylethylamine (13.9 mL, 81.6 mmol) and dichloromethane (80 mL) was cooled to 0° C. and then a solution of 3-methoxy-4-nitrobenzoyl chloride (11.76 g, 54.4 mmol) in dichloromethane (50 mL) was added dropwise. The mixture was allowed to warm to 23° C. over two hours, quenched with aqueous hydrochloric acid (3M, 20 mL), washed with water (3×20 mL), dried (Na2SO4) and concentrated in vacuo to provide N-[2-(2-methoxyphenoxy)ethyl]-3-methoxy-4-nitrobenzamide (14 g, 74% yield) an off white solid; MS (PB-PCI) C17H18N2O6 m/e calc 346.34; found 347 (MH+). quenched with aqueous hydrochloric acid (3M, 20 mL) washed with water (3×20 mL) dried (Na2SO4) concentrated in vacuo

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: tert-Butyl 2-(2-methoxyphenoxy)ethylcarbamate (23.8 g, 89 mmol) was cooled to 0° C. and stirred as a mixture of trifluoroacetic acid:dichloromethane (1:1, 40 mL) was added dropwise. The mixture was allow to warm to 23° C., stirred for 2 hours and concentrated in vacuo. The residue was taken back up in dichloromethane (100 mL) and the solution was washed with saturated aqueous sodium hydrogen carbonate (3×20 mL) and aqueous sodium hydroxide (10%, 3×20 mL), dried (Na2SO4), filtered and concentrated in vacuo to provide 2-(2-methoxyphenoxy)ethylamine (13 g, 88% yield) a light yellow solid; MS (PB-PCI) C9H13NO2 m/e calc 167.21; found 168 (MH+). was added dropwise concentrated in vacuo the solution was washed with saturated aqueous sodium hydrogen carbonate (3×20 mL) and aqueous sodium hydroxide (10%, 3×20 mL) dried (Na2SO4) filtered concentrated in vacuo

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

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

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

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