Hydrochloric Acid → HCID 178455728, compound

Temperature

70 °C

To a solution of 3.68 g of 1-bromomethyl-4-ethynylcyclohexane (trans/cis=about 3/1) in 20 mL of N,N-dimethylformamide were added 3.13 g of 3,3,3-trifluoropropylmalononitrile, 3.21 g of potassium iodide and 2.67 g of potassium carbonate, followed by stirring at 70° C. for 5 hours. The reaction mixture was cooled to room temperature and then 50 mL of a 1 N aqueous hydrochloric acid solution was added thereto. The reaction mixture was extracted three times with 30 mL of ethyl acetate. The combined organic layer was washed sequentially with 100 mL of a saturated aqueous sodium hydrogen carbonate solution and 100 mL of a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 3.20 g of the trans isomer (hereinafter referred to as the present compound (1t)) and 1.01 g of the cis isomer (hereinafter referred to as the present compound (1c)) of 1-(2,2-dicyano-5,5,5-trifluoropentyl)-4-ethynylcyclohexane (hereinafter referred to as the present compound (1)) represented by the following formula:

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionThe reaction mixture was extracted three times with 30 mL of ethyl acetate
3. washThe combined organic layer was washed sequentially with 100 mL of a saturated aqueous sodium hydrogen carbonate solution and 100 mL of a saturated aqueous sodium chloride solution
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customto give 3.20 g of the trans isomer (

ORD record

ord-e94e5c81d4e44be2aa07497cf4ccc943

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344163B2