tert-Butyl 4-(3-fluoroanilino)piperidine-1-carboxylate → N-(3-fluorophenyl)piperidin-4-amine

Participants

Reaction Steps

A solution of 1,1-dimethylethyl 4-[(3-fluorophenyl)amino]-1-piperidinecarboxylate (D3) (2.30 g) in 2M HCl (5 ml) and 1,4-dioxane (40 ml) was heated at 70° C. with stirring overnight. On cooling, the solvent was removed in vacuo and the residue diluted with 2M NaOH solution and extracted with 9:1 EtOAc/tBuOH (×2). The organics were dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow solid (1.33 g). δH (CDCl3, 250 MHz) 7.07 (1H, q), 6.33 (3H, m), 3.83 (1H, br s), 3.33 (1H, br s), 3.12 (2H, m), 2.71 (2H, m), 2.04 (2H, m), 1.30 (2H, m).

Provenance & Evidence