Hydrochloric Acid → N-(2,2,2-Trifluoroethyl)dodecan-1-amine

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Reaction Steps

A solution of 8 ml. BH3 in THF (8 mM) is added dropwise to a solution of 1.12 g. (4 mM) dodecyl-trifluoroacetamide in 6 ml. THF at 0° C. under N2. The mixture is refluxed 16 hours, cooled in ice, and 6 ml. concentrated HCl added slowly. The THF is distilled off at atmosphere pressure, the mixture cooled in ice, and solid NaOH added slowly with cooling until alkaline to pH paper. The aqueous solution is then extracted three times with hexane. The combined organic layers are washed with water, dried over K2CO3, filtered, stripped to give 2.0 g. crude product. It is then chromatographed in cyclohexane/EtOAc (10:1) on silica gel (Rf =0.4) to give 870 mg. oil which is distilled at 0.3 mM., b.p. 135° C., to give 405 mg. pure product, 38% yield. NMR (CDCl3, δ): 3.22 q, J=10 (2H); 2.79 m (2H); 1.40 s (20H); 0.93 m (3H). IR shows no carbonyl bands.

Provenance & Evidence