Triethylamine → 5-Indanyl isocyanate

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To a solution of 5-aminoindane (25 g) in anhydrous diethyl ether (1250 ml), under an atmosphere of nitrogen, at 0° C. was added triphosgene (18.3 g). The mixture was stirred at 0° C. for 2 min then triethylamine (64.7 ml) was added until pH8. The mixture was stirred at 0° C. for 10 min then at. 10° C. for 10 min. The undissolved solids were filtered off and the filtrate evaporated in vacuo. The residue was distilled at 100° C./1 mbar to afford the title compound (20 g). 1H NMR (360 MHz, CDCl3) δ2.07 (2H, quin, J=7.5 Hz), 2.86 (4H, m), 6.84 (1H, dd, J=7.9 and 2.0 Hz), 6.94 (1H, s), 7.13 (1H, d, J=7.9 Hz).

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