(S)-1,4-dibenzyl-2-(2-methoxy-ethyl)-piperazine → (S)-2-(2-Methoxyethyl)piperazine

HRID 131393Notes

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]1

Participants

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).

Workup

customAdd palladium hydroxide (Pearlman's catalyst, 400 mg), purge vessel with nitrogen
temperatureAllow the mixture to cool to ambient temperature
filtrationFilter off the catalyst
washrinse with ethanol (5 mL)
concentrationConcentrate in vacuo
customusing a 35° C.

Sources & evidence

ORD record: ord-298b650da7e94be79745a4091c7a05f9
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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