(S)-1,4-dibenzyl-2-(2-methoxy-ethyl)-piperazine → (S)-2-(2-Methoxyethyl)piperazine
Reaction equation
C([N:8]1[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][C@@H:9]1[CH2:21][CH2:22][O:23][CH3:24])C1C=CC=CC=1>C(O)C>[CH3:24][O:23][CH2:22][CH2:21][C@H:9]1[CH2:10][NH:11][CH2:12][CH2:13][NH:8]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Dissolve (S)-1,4-dibenzyl-2-(2-methoxy-ethyl)-piperazine (2.0 g, 6.2 mmol) in ethanol (15 mL) in a suitable hydrogenation vessel. Add palladium hydroxide (Pearlman's catalyst, 400 mg), purge vessel with nitrogen, then pressure to 60 psi. Heat to 50° C. and stir vigorously for 18-24 hours. Allow the mixture to cool to ambient temperature. Filter off the catalyst and rinse with ethanol (5 mL). Concentrate in vacuo using a 35° C. bath to afford the title compound (0.81 g, 91.1%). 1H NMR (500 MHz, DMSO-d6) δ 1.41 (m, 2H), 2.12 (t, 1H), 2.43 (td, 1H), 2.53 (m, 2H, 1H), 2.63 (d, 1H), 2.72 (m, 2H), 3.19. (s, 3H), 3.34 (m, 2H).