Isobutylamine → 4-[3-(Isobutylamino)-2-hydroxypropoxy]aniline

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Reaction Steps

Isobutylamine (5.1 ml, 51.2 mmol) was added to a solution of 4-(2,3-epoxypropoxy) nitrobenzene (obtained as described in Synthetic Communications, 1994, 24, 833; 1.0 g, 5.12 mmol) in THF (1 ml). The solution was heated under reflux for 3 hours and then volatile material was removed by evaporation. The residue was dissolved in methanol (5 ml) and 10% palladium on carbon (0.50 g) and ammonium formate (3.23 g, 51.2 mmol) were added. The mixture was heated under reflux for 3 hours and then filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure to give the product as dark brown oil (1.22 g, 100%), which was used without further purification. MS (MH+): 238.9.

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