1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-{2-[4-(4-Chlorophenoxy)piperidin-1-yl]-2-oxoethyl}-3,3-diphenylpiperidin-2-one

Participants

Reaction Steps

To a solution of the product of Example 68E (117 mg, 0.38 mmol), 4-(4-chlorophenoxy)piperidine (80.0 mg, 0.378 mmol), and 4-(dimethylamino)pyridine (4.6 mg, 0.038 mmol) in CH2Cl2 (2 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.067 mL, 0.378 mmol) via syringe. The reaction was stirred at ambient temperature for 45 hours. The reaction mixture was diluted with 50 mL CH2Cl2, then washed with 1 N aqueous HCl, saturated aqueous NaHCO3 solution and brine, dried with Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica gel (Analogix® Intelliflash™ 280; SF15-24 g column; 50% ethyl acetate/hexanes) which yielded the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.36-7.17 (m, 12H), 6.86-6.80 (m, 2H), 4.55-4.45 (m, 1H), 4.40 (d, J=15.6, 1H), 4.09 (d, J=15.6, 1H), 3.80-3.33 (m, 6H), 2.72-2.57 (m, 2H), 2.00-1.74 (m, 6H); MS (ESI+) m/z 503 (M+H)+.

Provenance & Evidence