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

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.

1. customat 0° C.
2. temperatureThe mixture is refluxed 16 hours
3. temperaturecooled in ice
4. distillationThe THF is distilled off at atmosphere pressure
5. temperaturethe mixture cooled in ice
6. additionsolid NaOH added slowly
7. temperaturewith cooling until alkaline
8. extractionThe aqueous solution is then extracted three times with hexane
9. washThe combined organic layers are washed with water
10. dry with materialdried over K2CO3
11. filtrationfiltered
12. customto give 2.0 g
13. customIt is then chromatographed in cyclohexane/EtOAc (10:1) on silica gel (Rf =0.4)
14. customto give 870 mg
15. distillationoil which is distilled at 0.3 mM
16. custom, b.p. 135° C., to give 405 mg

ORD record

ord-734cb9a3277a4deca7a74b085c71f846

Source dataset

uspto-grants-1988_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04719312