Sodium Hydroxide → 2-Phenylpiperazine

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To a solution of 2-phenylpyrazine (11.64 gram, 74.53 mmol) in acetic acid (58.2 ml) was added palladium acetate Pd(OAc)2 (2.33 gram, 9.94 mmol). The mixture was hydrogenated at 50 psi for four hours. After the reaction was complete, the catalyst was filtered off and rinsed with a small portion of acetic acid. The filtrate was concentrated under house vacuum to give a brown-black solid which was suspended in deionized water (300 ml) and adjusted to pH 13 with 20% NaOH solution. The product was extracted from aqueous solution with EtOAc (200 ml, 3×), dried over MgSO4, filtered and evaporated to dryness to give 2-phenylpiperazine (7.2 gram). An additional 1.6 g of 2-phenylpiperazine was obtained by evaporating the aqueous fraction to a solid and triturating the solid with CH2Cl2. Total yield of 2-phenylpiperazine was 73%. The crude material was crystallized from EtOAc and hexane for characterization, m.p. 86°-88° C.; FAB mass [M+1]+ 163; Found, C, 74.04; H, 8.66; N, 17.15. Calcd. for C10H14N2, C, 74.04; H. 8.69; N, 17.26.

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