HCID 19420474, compound → 1-[(Naphthalen-1-yl)methyl]piperazine

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Reaction Steps

Following the procedure of Example 6, but replacing 1-benzylpiperazine with 1-β-naphthylmethylpiperazine, provided the desired compound. To a solution of piperazine (2.0 g, 0.023 mol) in 15 mL of ethanol added a solution of (2-bromomethyl)naphthalene (5 g, 0.023 mol) in 15 mL of warm ethanol. It was stirred at 55° C. for 1 hour and stirred at room temperature for one over night. The resulting precipitate was filtered, washed with ethyl acetate (20 mL×2), and dried to yield 1-naphthylmethylpiperazine hydrobromide (2.3 g). MS m/z M+H=227, H1 -NMR (in MeOH-d4) δ=2.85 (t, 4H, piperazine), 3.20 (t, 4H, piperazine), 3.72 (s, 2H, benzyl), 7.45 (m, 3H, aromatic), 7.70 (s, 2H, aromatic), 7.80 (3, 3H, aromatic). The obtained 1-naphthylmethylpiperazine hydrobromide (2.2 g, 7.16 mmol) was dissolved in 50 mL of 3 N sodium hydroxide aqueous solution and stirred at room temperature for 30 minutes. The product was extracted with ethyl acetate (50 mL×3), and the combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate. Solvent was removed to obtain 1.2 g of 1-[naphthylmethyl]piperazine in 75% yield. MS m/z M+H=227, H1 -NMR (in MeOH-d6) δ=2.5 (m, 4H, piperazine), 2.95 (t, 4H, piperazine), 3.55 (s, 2H, benzyl), 7.74 (m, 3H, aromatic), 7.72 (s, 2H, aromatic), 7.79 (m, 3H, aromatic).

Provenance & Evidence