Potassium Hydroxide → 2-Amino-5,5,6,6,6-pentafluorohexanenitrile

Temperature

25 °C

A solution of 1,1,1,2,2-pentafluoro-4-iodobutane (2.00 g, 7.30 mmol) in CH2Cl2 (5.99 mL), potassium hydroxide (11 N aq.) (11.95 mL, 131 mmol) and benzyltriethylammonium chloride (0.166 g, 0.730 mmol) were added to a stirred solution of N-(diphenylmethylene)aminoacetonitrile (1.608 g, 730 mmol) in DCM (6 mL) at 25° C. The resulting two-phase mixture was stirred at 25° C. for 4 days. The organic phase was separated, dried (Na2SO4) and concentrated in vacuo. The resulting residue was mixed with Et2O (72 mL) and 1N aq. HCl (72 mL) and stirred at room temperature for 2 days. The aqueous layer was separated and made alkaline with 5N aq. NaOH solution and the resulting oil was taken up in DCM. The organic phase was dried (Na2SO4) and concentrated in vacuo to afford the desired product, as an oil. 1H NMR (500 MHz, CHCl3-d): δ 3.75 (br s, 1H); 2.41-2.17 (m, 2H); 2.11-4.97 (m, 2H); 1.50 (br s, 2H). m/z=203.2 (M+H).

1. customThe organic phase was separated
2. dry with materialdried (Na2SO4)
3. concentrationconcentrated in vacuo
4. additionThe resulting residue was mixed with Et2O (72 mL) and 1N aq. HCl (72 mL)
5. stirringstirred at room temperature for 2 days
6. customThe aqueous layer was separated
7. dry with materialThe organic phase was dried (Na2SO4)
8. concentrationconcentrated in vacuo

ORD record

ord-57427aac73ea480dad68a7b1f88aea7a

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365574B2