Hydrochloric Acid → Dimyristylamine

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N-myristyl myristamide (0.90 g; 2.1 mmole) was treated with borane THF (5 mL of 1 M solution, 5.0 mmole) and reacted at reflux for 3 hrs. The reaction mixture was carefully neutralized with 3N HCl aqueous solution and stirred at 50° C. for 20 min., the back neutralized with 2N NaOH aqueous solution. The mixture was concentrated, then partitioned between CH2Cl2 and saturated NaHCO3 aqueous solution, dried and concentrated, affording 0.93 g of product. NMR (CDCl3): δ2.59 (t, 2H, J=7.2 Hz), 1.40-1.55 (m, 2H), 1.15-1.40 (m, 22H), 0.88 (t, 3H, J=6.8 Hz).

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