Acetic Acid → N-Cyclohexyl-1,2-ethanediamine

To a solution of cyclohexanone (6.260 g, 63.8 mmol), ethylenediamine (42.640 mL, 637.8 mmol), acetic acid (36.515 mL, 637.8 mmol), and 4 {acute over (Å)} molecular sieves (25 g) in anhydrous methanol (250 mL) was added sodium cyanoborohydride (8.017 g, 127.6 mmol). The mixture was stirred for 48 hrs, filtered to remove the solids, and concentrated in vacuo. The residue was dissolved in 3 N aqueous sodium hydroxide (150 mL) and extracted with methylene chloride (3×300 mL). The combined organic layers were washed with basic saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated to give the crude product. The material was vacuum distilled to give the desired product as a clear liquid (4.1 g, 45%). 1H NMR (300 MHz, CDCl3) δ 2.80-2.76 (td, 2H, J=0.9, 6.0 Hz), 2.68-2.64 (td, 2H, J=0.9, 6.0 Hz), 2.43-2.34 (m, 1H), 1.89-1.83 (m, 2H), 1.74-1.70 (m, 2H), 1.62-1.57 (m, 1H), 1.32-0.98 (m, 8H).

1. filtrationfiltered
2. customto remove the solids
3. concentrationconcentrated in vacuo
4. dissolutionThe residue was dissolved in 3 N aqueous sodium hydroxide (150 mL)
5. extractionextracted with methylene chloride (3×300 mL)
6. washThe combined organic layers were washed with basic saturated aqueous sodium chloride
7. dry with materialdried (anhydrous sodium sulfate)
8. filtrationfiltered
9. concentrationconcentrated
10. customto give the crude product
11. distillationdistilled

ORD record

ord-8462f7971b6845c0bee83a274715b6e9

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09265772B2