4-Nitrophenol → 1-[3-(4-Nitrophenoxy)propyl]piperidine

Participants

Reaction Steps

In a three-neck flask with an overhead mechanical stirrer, a mixture of 1-(3-chloropropyl)-piperidine (49.8 g, 0.308 mol), 4-nitrophenol (42.8 g, 0.308 mol) and K2CO3 (212 g, 1.53 mol), in anhydrous DMF (200 mL) was heated to 94° C. and stirred for 18 h. The mixture was cooled to RT then diluted with 2 L water. The organics were taken up in EtOAc (2 L) and washed twice with 2N NaOH (500 mL) then brine (200 mL). The combined organics were dried over anhydrous MgSO4 then concentrated under reduced pressure to give 1-[3-(4-nitro-phenoxy)-propyl]-piperidine as a yellowish oil.

Provenance & Evidence