Piperidine → HCID 11952155, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−23° C.) solution of {2-[4-(3-piperidin-1-ylpropoxy)phenyl]-4,5-dihydro-1,3-oxazol-4-yl}methanol ax46 (0.27 g, 0.85 mmol, 1 eq) and triethylamine (0.413 ml, 2.98 mmol, 3.5 eq) in tetrahydrofuran (10 ml) is added methanesulfonyl chloride (0.23 ml, 2.98 mmol, 3.5 eq). The mixture is stirred for 2 h at −23° C., and then, concentrated under vacuum. The residual oil is treated with piperidine (0.08 ml, 0.8 nmol, 2 eq) and triethylamine (0.05 ml, 0.42 mmol, 1 eq) and stirred at 100° C. in a sealed tube overnight. After 24 h, piperidine (1 eq) and triethylamine (1 eq) are added and the mixture is stirred for another 48 h at 100° C. Concentration under vacuum gives 0.33 g of brown oil. The oil is purified on silicagel (eluent: dichloromethane/ethanol/ammonia 92:7.2:0.8) to give 45 mg of 1-(3-{4-[4-(piperidin-1-ylmethyl)-4,5-dihydro-1,3-oxazol-2-yl]phenoxy}propyl)piperidine 20.

Provenance & Evidence