Sodium Iodide → 8-(4-Methylpiperazin-1-yl)naphthalen-2-ol

Participants

Reaction Steps

To a stirring solution of 8-amino-2-naphthol (3.28 g, 20 mmol, Aldrich Chem. Co.) in 100 mL of acetonitrile was added sodium bicarbonate (7.42 g, 88 mmol), sodium iodide (6.72 g, 44 mmol) and mechlorethamine hydrochloride (4.32 g, 22 mmol). Under nitrogen, the reaction was heated to reflux and stirred for another 2 hr. The reaction mixture was then allowed to cool to room temperature and was stirred overnight. A thin layer chromatography (tlc) using methylene chloride: methanol: conc. ammonium hydroxide (90:10:1) showed the more polar product (Rf 0.25) with only a trace of the starting naphthol. Silica gel (4.5 g) was added and the reaction mixture was concentrated in vacuo to a dry purple solid. This was added to a column of silica gel (ca. 400 g) and eluted with 2 L volumes of CH2Cl2, CH2Cl2 :CH3OH (40:1), CH2Cl2 :CH3OH:conc. NH4OH (20:1:0.1) and finally 4 L of CH2Cl2 :CH3OH:conc. NH4CH (10:1:0.1). The appropriate fractions were combined to yield a purple-black solid, 5.26 g, mp 184°-185° C.

Provenance & Evidence