Triphenylphosphine → morpholino(5-(3-(piperidin-1-yl)propoxy)-1H-indol-2-yl)methanone

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Reaction Steps

A mixture of 246 mg (1 mmol) (5-hydroxy-1H-indol-2-yl)-morpholin-4-yl-methanone, 1 g (ca. 3 mmol) polymerbound triphenylphospine (Fluka), 179 mg (1.25 mmol) piperidinepropanol and 461 mg (2 mmol) di-tert.-butyl azadicarboxylate in 20 ml THF was stirred for a prolonged period of time at room temperature. The mixture was filtered through a pad of silica and washed with 30 ml THF. The mixture was evaporated to dryness and purified on silica eluting with a gradient of DCM/2N NH3 in methanol 98/2 to DCM/2N NH3 in methanol 9/1. The product fractions were evaporated and the residue was titurated with diethyl ether to yield after drying at 40° C. under vacuum 47 mg (13%) of the title compound as white solid. MS (m/e): 372.4 (MH+, 100%).

Provenance & Evidence