1-Nitropropane → N,N-dimethyl-2-(3-cyanoindol-5-yl)cycloprop-1-yl methylamine

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Reaction Steps

In 5 mL of acetic acid was combined 120 mg of crude N,N-dimethyl-2-(3-formyl-indol-5-yl)cycloprop-1-yl-methylamine, ammonium hydrogen phosphate (0.48 g, 3.62 mmol, 7.3 equiv.), and nitropropane (0.04 mL, 0.5 mmol, 1 equiv.). The mixture was stirred and heated to a gentle reflux for 16 h. Water was added after cooling reaction to room temperature, and the mixture was made basic by the addition of 1 N NaOH. The mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give N,N-dimethyl-2-(3-cyanoindol-5-yl)cycloprop-1-yl methylamine (90 mg, 75%) as a brown oil. The oil was purified by flash chromatography to give a brown solid with 92% purity by reverse-phase HPLC. 1H NMR (MeOH-d4): δ 7.88 (s, 1H), 7.40 (d, J=7.5 Hz, 1H), 7.36 (d, J=1.9 Hz, 1H), 7.04 (dd, J=8.5, 1.7 Hz, 1H), 2.62 (dd, J=7.3 Hz, 1H), 2.42 (m, 1H), 2.38 (s, 6H), 1.89 (m, 1H), 1.20 (m, 1H), 1.08 (m, 1H), and 0.90 (m, 1H). IR: 2214.5 cm−1. FIMS: 238.2 (M−H)−.

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