Dimethylformamide → 1-(4-(piperidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea

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Reaction Conditions

Reaction Steps

(4-(piperidin-1-yl)phenyl)methanamine 2m (1.47 g, 7.8 mmol) was dissolved in 40 ml of AcOEt and at 0° C. triphosgene (2.3 g, 1 equiv.) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 20 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (1.15 g, 7.8 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1×30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 520 mg of a pale yellow solid. Yield=18% 1HNMR (DMSO, 200 MHz) δ 1.58 (6H, m), 3.08 (4H, m), 4.19 (2H, d, J=6 Hz), 6.62 (2H, m), 6.86 (4H, m), 7.15 (2H, d, J=8.8 Hz), 8.19 (1H, bs), 9.95 (1H, bs), 10.58 (1H, bs); [M+1] 366.3 (C20H23N5O2 requires 365.43).

Provenance & Evidence