1-Benzyl-3-(trifluoromethyl)piperazine → 2-(Trifluoromethyl)piperazine

Reaction equation

C([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([C:14]([F:17])([F:16])[F:15])[CH2:9]1)C1C=CC=CC=1>C(O)(=O)C.O.[Pd]>[F:15][C:14]([F:17])([F:16])[CH:10]1[CH2:9][NH:8][CH2:13][CH2:12][NH:11]1

Participants

Procedure

1-Benzyl-3-(trifluoromethyl)piperazine (0.74 g, 3.0 mmol; Intermediate 44) was dissolved in acetic acid (70 mL) and water (5 mL). Pd, 5% on carbon, (0.074 g) was added and =hydrogenation was performed at 3 bar and 70° C. overnight. The reaction mixture was filtered through Celite and the pad was rinsed with water (5 mL). Solvents were removed in vacuo, toluene (20 mL) added to the residue, followed by re-concentration in vacuo to remove residual water. The desired product sublimated on the evaporator and 0.15 g (32%) was collected as a white powder. 1H NMR (270 MHz, methanol-d4) δ ppm 2.67-2.87 (m, 3H) 2.91-3.05 (m, 2H) 3.12-3.21 (m, 1H). MS (ESI+) m/z 155. *Previously described in Rec. Trav. Chim. Pays-Bas 1995, 114, 97-102.