1-((1R,2R)-2-(1-benzylpiperidin-3-ylamino)cyclohexyl)-3-phenylurea → 1-phenyl-3-((1R,2R)-2-(piperidin-3-ylamino)cyclohexyl)urea

Participants

Reaction Steps

To a PARR shaker was added 1-((1R,2R)-2-(1-benzylpiperidin-3-ylamino)cyclohexyl)-3-phenylurea (1.4 g, 3.44 mmol), Pd(OH)2 (0.484 g, 3.44 mmol), MeOH (20 mL) and 3 drops of 1N HCl. The reaction vessel charged with hydrogen and the pressure was maintained at 30 psi with shaking overnight. After this time, the reaction was filtered through CELITE® and the filtrate was concentrated to give the product, 1-phenyl-3-((1R,2R)-2-(piperidin-3-ylamino)cyclohexyl)urea (1.05 g, 3.32 mmol, 96% yield), as an off white solid. It was used in the next step without further purification. Anal. Calcd. for C18H28N4O m/z 316, found: 317.3 (M+H)+; 1H NMR (500 MHz, methanol-d3) δ ppm 7.35 (d, J=7.70 Hz, 2H), 7.24 (t, J=7.42 Hz, 2H), 6.97 (t, J=7.42 Hz, 1H), 3.49-3.37 (m, 1H), 3.16-3.03 (m, 1H), 2.94-2.83 (m, 1H), 2.70 (td, J=9.35, 4.95 Hz, 1H), 2.57-2.47 (m, 1H), 2.47-2.39 (m, 1H), 2.39-2.25 (m, 1H), 2.10-1.90 (m, 3H), 1.79-1.68 (m, 3H), 1.58-1.43 (m, 1H), 1.39-1.16 (m, 5H).

Provenance & Evidence