1H-Indole-3-carbonyl chloride → N-((quinuclidin-4-yl)methyl)-1H-indole-3-carboxamide

Participants

Reaction Steps

To a solution of 1H-indole-3-carbonyl chloride (112 mg, 0.625 mmol) in 3 mL of methylene chloride at 0° C. was added (quinuclidin-4-yl)methanamine (86 mg, 0.614 mmol) in 2 mL of methylene chloride. The mixture was stirred at room temperature overnight. The solvent was evaporated and water (20 mL) was added. The water layer was basified to pH 12 with 10% aqueous potassium hydroxide and extracted three times with 25 mL each of ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to yield 26 mg of the desired product. 1HNMR: 11.6 (bs, 1H); 8.15 (m, 1H); 8.13 (bs, 1H); 7.65 (bs, 1H); 7.42 (d, 1H); 7.15 (m, 2H); 3.1 (m, 2H); 2.65 (m, 6H); 1.40 (m, 6H). MS (m/e): 284.

Provenance & Evidence