Triethylamine → HCID 46222161, compound

Participants

Reaction Steps

To a solution of N-isopropyl indole (100 mg, 0.63 mmol) in diethyl ether (2 mL) at 0° C. was drop-wise added oxalyl chloride (60 mL, 0.73 mmol). The mixture was allowed to warm to room temperature over a period of three hours and then concentrated in vacuo to give a yellow solid. To the yellow solid was added dichloromethane (2 mL), triethyl amine (0.525 mL, 3.77 mmol), and a solution of the crude 2-(4-butylpiperidin-1-yl)ethanamine (150 mg) in triethyl amine (0.525 mL, 3.77 mmol) and dichloromethane (1 mL). The mixture was stirred at room temperature for 66 hours, then washed with saturated aqueous sodium bicarbonate (1×5 mL) and water (1×5 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give a yellow oil, which was purified by silica chromatography on a Biotage (2-10% MeOH/CH2Cl2) to give a yellow gum (6 mg, 2% yield): 1H NMR (400 MHz, CDCl3): δ 9.11 (s, 1H), 8.46 (m, 1H), 7.92 (t, 1H), 7.43 (m, 1H), 7.33 (m, 2H) 4.71 (m, 1H), 3.47 (q, 2H), 2.45 (d, 2H), 2.54 (t, 2H), 1.98 (t, 2H), 1.65 (m, 2H), 1.61 (d, 6H), 1.25 (m, 9H), 0.89 (t, 3H); MS (ESI) m/z: Calculated for C24H35N3O2: 397.3. Found: 398.3 (M+H)+.

Provenance & Evidence