Acetic Anhydride → Acetamide,n-[4-(6-amino-4-methyl-2-pyridinyl)butyl]-

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Reaction Steps

Triethylamine (0.059 mL, 43 mg, 0.42 mmol) and acetic anhydride (0.029 mL, 31 mg, 0.031 mmol) were added to a solution of 50 mg (0.028 mmol) of 2-amino-6-(4-aminobutyl)-4-methylpyridine (from Example 56) in 1.0 mL of dichloromethane. The solution was allowed to stand for 48 h at room temperature, then diluted with 25 mL of ethyl acetate and washed with 12 mL of saturated aqueous sodium bicarbonate and 12 mL of saturated aqueous sodium chloride. The aqueous layers were extracted in succession with 15 mL of ethyl acetate. The combined organic layers were dried (sodium sulfate), decanted, and evaporated. The residue was purified by flash column chromatography on 3.5 g of silica gel, eluting with 100 mL of 5% methanol in dichloromethane to give 27 mg (44% yield of 6-(4-acetamidobutyl)-2-amino-4-methylpyridine as an oil which spontaneously crystallized.

Provenance & Evidence