4-[2-(3-Methoxy-4-nitrophenoxy)ethyl]morpholine → HCID 58748494, compound

Participants

Reaction Steps

To 4-[2-(3-methoxy-4-nitro-phenoxy)ethyl]morpholine (Intermediate 48; 16.97 g, 60 mmol, 1 eq) in ethanol (120 mL) was added 10% palladium on charcoal (850 mg, 5% wt). The reaction was stirred at room temperature for 19 hours. After filtering off the palladium residues the solvent was evaporated under reduced pressure. The product was dissolved in ethyl acetate (100 ml) and extracted twice with 2M HCl. The aqueous layers were combined, washed with ethyl acetate then basified by the addition of 2N NaOH. The basic layer was re-acidified and captured onto mp-TsOH resin. After washing several times with methanol the product was released using 10% ammonia in methanol. After evaporation in vacuo the title compound was obtained as a dark brown oil. (14.5 g, 89%)

Provenance & Evidence