1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-{2-oxo-2-[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethyl}-3-phenylpiperidin-2-one

Participants

Reaction Steps

To a solution of 7-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.056 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), and the reaction was stirred for approximately 39 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/hexane over 20 minutes (flow=30 mL/minute). The product was dissolved in a minimal amount of ethyl acetate, and hexanes were added which caused the product to precipitate. Concentration gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.16-7.48 (m, 8H), 4.80 (s, 1H), 4.71 (s, 1H), 4.48-4.57 (m, 1H), 4.09-4.23 (m, 1H), 3.78-3.99 (m, 1H), 3.68-3.79 (m, 2H), 3.54-3.67 (m, 1H), 3.40-3.54 (m, 1H), 2.90-3.03 (m, 2H), 2.13-2.30 (m, 1H), 1.93-2.11 (m, 2H), 1.76-1.96 (m, 1H); MS (ESI+) m/z 417 (M+H)+.

Provenance & Evidence