Hydrazine hydrate (1:1) → 2-n-Octyl-1-dodecylamine

Participants

Reaction Conditions

Reaction Steps

Iodoalkane 5 (5.90 g, 14.5 mmol) and potassium phthalimide (2.94 g, 15.9 mmol) were taken up in 25 mL of DMF and vigorously stirred for 72 hours at 25° C. The reaction mixture was then taken up in 200 mL of pentane, washed four times with 100 mL of water, passed through a 3 cm silica gel plug, and concentrated to give a colorless oil. The oil was next taken up in 150 mL of ethanol, 4 mL of hydrazine hydrate was added, and the mixture was heated at reflux overnight. The resulting precipitate was collected by filtration, dissolved in 100 mL of water, and the solution was made alkaline by the addition of 6 M NaOH (aq). The resulting mixture was then taken up in 200 mL of pentane, washed four times with 100 mL of water, once with 70 mL of brine, and concentrated to give a colorless oil (3.08 g, 72% yield). Anal. Calcd. for C20H43N: C, 80.73; H, 14.57. Found: C, 80.78; H, 14.52; 1H NMR (CDCl3): 2.60 (d, J=5.0 Hz, 2H), 2.00 (t, J=5.0 Hz, 1H), 1.30-1.20 (b, 32H), 0.89 (t, J=7.5 Hz, 6H); MS (EI): m/z (%) 297.34 (100) [M+].

Provenance & Evidence