C([N:8]1[CH2:17][C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:18].[H][H]>O1CCOCC1.[Pd]>[ClH:18].[N:15]1[C:16]2[CH2:17][NH:8][CH2:9][CH2:10][C:11]=2[CH:12]=[CH:13][CH:14]=1A methanolic solution (25 mL) of 7-Benzyl-5,6,7,8-tetrahydro-[1,7]naphthyridine (J. Het. Chem. 2001, 38, 535) (1.5 g, 6.69 mmol) was degassed with argon for 20 min followed by the addition of 4N HCl in dioxane (2 mL) and Pd/C (300 mg, 20 wt %) and stirred under 50 psi hydrogen pressure at room temperature for 24 h. After completion of the reaction the mixture was filtered on a short pad of celite and washed with methanol (4×25 mL). The filtrate was evaporated to dryness in vacuo and crystallized from methanol to afford the title compound as yellowish solid in 65% yield (calculated as 2HCl salt), 900 mg.
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