Water → HCID 18789888, compound

Participants

Reaction Steps

A portion (15.63 g, 0.040 mol) of the 1-(2-chloro-4-nitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane produced in (2) above was dissolved in hot ethanol (500 ml) and, thereafter, a solution consisting of a mixture of Na2S2O4 (27.56 g) and water (125 ml) was added to the resulting solution, thereby forming a precipitate. The mixture was heated at the reflux temperature for 20 min. Thereafter, the solvent was evaporated and the residue was diluted with water, followed by extraction with ethyl acetate. An aqueous solution of sodium carbonate was added to the aqueous layer such that it became basic up to a pH of about 9, followed by three extractions with ethyl acetate. The organic extracts were combined, dried with magnesium sulfate, and the solvent was evaporated; thereafter, the residue was purified by being subjected to column chromatography on silica gel using, as an eluent, ethyl acetate containing methanol (10%). The fractions containing the end compound were combined and the solvent was evaporated to yield the end compound 1-(4-amino-2-chlorophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane (4.78 g) as a yellow oil.

Provenance & Evidence