Trifluoroacetic acid → O-Benzyl-N-(4-cyanobutyl)hydroxylamine

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Reaction Steps

N-(4-Cyanobutyl)-O-benzylhydroxylamine (5) was synthesized by adding trifluoroacetic acid (TFA, 16 mL) to (4) (2.59 g, 8.51 mmol), and the solution was stirred at room temperature for 20 minutes (Drierite tube). Excess TFA was removed by rotary evaporation, saturated NaHCO3 (50 mL) was added and the product was extracted into ether (3×50 mL). After a brine wash (50 mL), the organic extracts were concentrated to yield 1.77 g crude product. Column chromatography with 3% EtOH/CHCl3 furnished 1.31 g of (5) (75% yield): NMR δ 1.5-1.7 (m, 4 H), 2.16-2.35 (m, 2 H), 2.78-2.98 (m, 2 H), 4.66 (s, 2 H), 5.45 (br s, 1 H), 7.28 (s, 5 H). Anal. calcd. for C12H16N2O: C, 70.56; H, 7.90. Found: C, 70.51; H, 7.91.

Provenance & Evidence