Hydrochloric Acid → 1-(2-Fluoroethyl)-4-(4-piperidinyl)piperazine trihydrochloride

Participants

Reaction Steps

1,1-Dimethylethyl 4-[4-(2-fluoroethyl)-1-piperazinyl]-1-piperidinecarboxylate (28.95 g, 91.78 mmol) was dissolved in 76 mL of MeOH and 76 mL 37% HCl was added. Reaction was stirred for 3 h and then concentrated in vacuo and to give 1-(2-fluoroethyl)-4-(4-piperidinyl)piperazine trihydrochloride (˜29 g) which was then dissolved in DMSO (200 mL). K2CO3 (63 g, 459 mmol) was added followed by 4-fluoro-2-(methyloxy)-1-nitrobenzene (15.7 g, 91.8 mmol) and the reaction mixture was heated to 80° C. and allowed to stir overnight. The mixture was then poured into H2O and extracted with EtOAc (3×). The combined organics were dried with MgSO4, filtered, and concentrated in vacuo. The resulting solids were triturated with diethyl ether to give the title compound of step E (27.13 g, 81%). MS (M+H, ES+) 367.

Provenance & Evidence