Sodium borohydride → 3-(3',6'-Dihydro-[2,4'-bipyridin]-1'(2'H)-yl)propan-1-amine

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Reaction Steps

NaBH4 (2 g, 53 mmol) in small portions was added to a solution of 1-(3-aminopropyl)-4-[2-pyridyl]pyridinium bromide hydrobromide (6 g, 16 mmol) in MeOH (150 mL) at 0-5° C. over a period of 2 h. The reaction mixture was stirred overnight at room temperature and then the solvent was evaporated. The residue was suspended in ether (200 mL) and treated with aqueous 50% NaOH solution (100 mL). The ether layer was separated and the aqueous layer was extracted with additional ether (2×50 mL). The combined ether extracts were dried over potassium carbonate and the solvent was removed, giving 3-(3′,6′-dihydro-2′-H-[2,4′]bipyridinyl-1′-yl)propylamine (3.48 g) as an oil. The crude product was used in the next step immediately without further purification.

Provenance & Evidence