1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[1-(4-fluorophenyl)cyclobutyl]-2-(2-oxo-3-phenylpiperidin-1-yl)acetamide

Participants

Reaction Steps

To a solution of 1-(4-fluorophenyl)cyclobutanamine hydrochloride (0.048 g, 0.236 mmol) and 2-(2-oxo-3-phenylpiperidin-1-yl)acetic acid (Example 91D, 0.050 g, 0.214 mmol) in dichloromethane (0.5 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.049 mL, 0.279 mmol) (0.049 mL, 0.279 mmol), and the reaction was stirred for approximately 60 hours. The reaction was loaded directly onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). The product was dissolved in a minimal ethyl acetate and hexanes was added which caused the product to precipitate from solution. Concentration gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.34-7.43 (m, 2H), 7.22-7.34 (m, 3H), 7.14-7.20 (m, 2H), 7.09-7.11 (br s, 1H), 6.97-7.03 (m, 2H), 4.03 (d, J=14.1 Hz, 1H), 3.87 (d, J=14.1 Hz, 1H), 3.69 (dd, J=7.9, 6.0 Hz, 1H), 3.51-3.60 (m, 1H), 3.39-3.48 (m, 1H), 2.47-2.60 (m, 4H), 1.78-2.17 (m, 6H); MS (ESI−) m/z 379 (M−H)−.

Provenance & Evidence