Hydrochloric Acid → HCID 178526689, compound

Temperature

0 °C

Trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexanecarboxylic acid (1.63 g, 4.9 mmol, prepared in accordance with Example 42) was suspended in tetrahydrofuran (40 mL). The resulting suspension was cooled to 0° C. with an ice bath. Afterward, a solution of lithium aluminium hydride in tetrahydrofuran (4.9 mL, 1 M in THF) was added under stirring. The resulting solution was allowed to reach room temperature, and then sonicated for 3 hr. After allowing the mixture to react overnight at room temperature, the mixture was heated to 60° C. to ensure complete conversion of the starting material. After cooling to room temperature, the mixture was acidified with 1M HCl and then diluted with ethyl acetate (50 mL). This formed a precipitate. The suspension was centrifuged, and the supernatant was collected and washed with water (10 mL). The organic layer was washed with saturated aqueous ammonium chloride (20 mL), dried over magnesium sulfate, filtered, and concentrated under vacuum. The desired product was obtained as a solid (1.3 g, 83% yield).

1. customto reach room temperature
2. customsonicated for 3 hr
3. customto react overnight at room temperature
4. temperaturethe mixture was heated to 60° C.
5. temperatureAfter cooling to room temperature
6. customThis formed a precipitate
7. customthe supernatant was collected
8. washwashed with water (10 mL)
9. washThe organic layer was washed with saturated aqueous ammonium chloride (20 mL)
10. dry with materialdried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated under vacuum

ORD record

ord-f1cb20bfa3db46e3896c16ea82b3102e

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569495B2