Dibutylamine → Methyl 4-(3-(dibutylamino)propoxy)benzoate

Participants

Reaction Steps

A solution of the mixture of methyl 4-(3-bromopropoxy)benzoate [17a] methyl 4,4′-[1,3-propanediylbis(oxy)]bisbenzoate [20] previous step (19.12 g) and dibutylamine (27.14 g, 35.7 mL, 210 mmol) in toluene (50.0 mL) was stirred under reflux conditions for 3 hours, cooled and extracted with 15% hydrochloric acid (3×40 mL). The combined aqueous layers were washed with of toluene (50 mL), basified to pH 8.5 with sodium bicarbonate and extracted with toluene (3×30 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated under reduced pressure at 60° C. (water bath). The residue was dissolved in hexane and passed through thin layer of silica gel. The solvent was evaporated under reduced pressure at 50-60° C. (water bath) to give 14.71 g (61.1% yield from 2 steps) of methyl 4-(3-dibutylaminopropoxy)benzoate [18a] as an oil.

Provenance & Evidence