2-Indanone → ethyl 2-[(2,3-dihydro-1H-inden-2-yl)amino]acetate

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Reaction Steps

2-Indanone (25.1 g. 0.19 mol) and glycine ethyl ester hydrochloride (34.5 g, 0.247 mol) were dissolved in absolute ethanol (700 mL) and sodium cyanoborohydride (25.8 g, 0.41 mol) was added in portions to the solution. After addition the mixture was allowed to sit at room temperature overnight. The ethanol was removed under reduced pressure and the residue treated with water and extracted into ethyl acetate. The organic extract was repeatedly washed with saturated aqueous solutions of sodium bicarbonate and sodium chloride before being dried over magnesium sulfate and filtered. After the solvent was concentrated under vacuum an oil remained which was taken up in ether/ethanol (250/50 mL) and cooled by mean of an ice-water bath. Ether which had previously been saturated with anhydrous hydrogen chloride was slowly added to the solution. The precipitated product was filtered and washed with cold ether/ethanol to yield a white solid (21 g) melting at 166°-168° C.

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