Sodium Hydroxide → 5,6,7,8-Tetrahydro-3-methyl-7-(phenylmethyl)-2,7-naphthyridine-4-carbonitrile

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Reaction Steps

To a solution of (E)-3-amino-2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-but-2-enenitrile (15 g, 0.056 mole) in dichloromethane (200 mL), freshly prepared benzotriazol-1-ylmethylene-dimethyl-ammonium chloride (12 g, 0.068 mole) was added in one portion. The mixture was stirred for 24 h at ambient temperature. NaOH (2N, 200 mL) was added, and the resulting mixture was stirred vigorously for 5 min. The phases were separated and the aqueous phase was extracted with dichloromethane (100 mL). The combined organic phases were dried over magnesium sulfate, and the solvent was removed in vacuo. The crude product was purified by column chromatography to give 7-benzyl-3-methyl-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile as a colorless oil (8.9 g, 53% yield).

Provenance & Evidence