Pentachlorophenyl 4-(3-piperidin-1-ylpropoxy)benzoate → HCID 17986317, compound

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Reaction Steps

A mixture of pentachlorophenyl 4-(3-piperdin-1-ylpropoxy)benzoate (D10) (500 mg) and N-benzyl-4-fluoroisoindoline (D9) (200 mg) in IPA (10 ml) at rt was treated with poly(methylhydrosiloxane) (0.16 ml) and palladium hydroxide on carbon (30 mg, 20% Pd) and stirred overnight. The mixture was filtered and evaporated. The residue was redissolved in EtOAc (20 ml), washed with saturated sodium hydrogen carbonate solution (10 ml), water (2×10 ml), brine (10 ml), dried (MgSO4) and evaporated. The residue was chromatographed on a silica gel flash column [step gradient 2-8% MeOH (containing 10% 0.880 ammonia solution) in DCM]. The required fractions were evaporated, then redissolved in DCM and treated with excess 4M HCl in dioxan. The title compound (E55) (65 mg) was obtained by crystallisation from acetone. MS electrospray (+ion) 383 (MH+). 1H NMR δ (DMSO-d6): 10.15 (1H, m), 7.09-7.65 (7H, m),4.89 (4H, m), 4.13 (2H, t, J=6 Hz), 3.46 (2H, m), 3.16 (2H, m), 2.90 (2H, m), 2.22 (2H, m), 1.79 (5H, m), 1.42 (1H, m).

Provenance & Evidence