Triethylamine → but-2-ynyl 4-(1'-(dimethylcarbamoyl)-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]-1-yl)piperidine-1-carboxylate

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Reaction Steps

N,N-dimethyl-1-(piperidin-4-yl)-2′,3′-dihydrospiro[piperidine-4,4′-quinoline]-1′-carboxamide 2ae (35.7 mg, 0.1 mmol) was dissolved in acetonitrile (1 mL) and triethylamine (100 uL) and treated with but-2-ynyl carbonochloridate (26.5 mg, 0.2 mmol). The reaction was stirred for 1 hour, then diluted with methanol (0.5 mL) and purified by HPLC (2-99% CH3CN gradient, 0.05% TFA) to yield compound no. 5. LC/MS (10-99% CH3CN/0.05% TFA gradient over 5 min): m/z 453.2, retention time 2.31 minutes. 1H-NMR (CDCl3, 400 MHz): δ 12.65 (br s, 1H), 7.69 (d, J=6.9 Hz, 1H), 7.13 (t, J=8.3 Hz, 1H), 7.02 (t, J=8.1 Hz, 1H), 6.83 (d, J=9.2 Hz, 1H), 4.66 (s, 2H), 4.38 (br s, 2H), 3.58 (m, 2H), 3.45 (m, 2H), 3.31 (m, 1H), 3.08 (m, 5H), 2.85 (s, 6H), 2.37 (m, 2H), 1.97 (m, 2H), 1.86 (t, J=2.3 Hz, 3H), 1.81 (m, 3H), 1.42 (t, J=7.3 Hz, 2H).

Provenance & Evidence