Sodium hydride → 1-(3,4-dinitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane hydrochloride

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Reaction Steps

A portion (0.50 g, 2.1 mmol) of the 2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethanol produced in (1) above was dissolved in dimethyl sulfoxide (6 ml) and 60% sodium hydride (0.12 g, 3 mmol) was added to the resulting solution. The reaction mixture was stirred at room temperature for 1 h and 1-chloro-3,4-dinitrobenzene (0.48 ml, 4 mmol) was added on a water bath. The mixture was stirred at room temperature for 2 h and after adding a saturated aqueous solution of sodium bicarbonate, three extractions were conducted with chloroform. The organic layers were combined, dried with sodium sulfate and concentrated under vacuum. The residue was purified by being subjected to column chromatography on silica gel using a 15:1 solvent system of chloroform and methanol as an eluent and the fractions containing the end compound were collected and the solvent was evaporated under vacuum, with the residue being recrystallized from ethanol to yield the titled compound 1-(3,4-dinitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane hydrochloride (0.31 g).

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