Hydrochloric Acid → HCID 11469684, compound

Temperature

5 °C

To a 5° C. solution of dimethylaniline (320 ml, 2.54 mol) in t-butyl alcohol (480 ml) was added dropwise a solution of cyclohexyl-acetyl chloride (250.9 g, 1.56 mol) in dichloromethane (320 ml) over 30 min. At the end of the addition, the addition funnel was rinsed with dichloromethane (80 ml). The reaction mixture was stirred 90 min at 5° C. and then allowed to warm to room temperature. After 15 hours at room temperature, the reaction solution was heated to reflux for 6 hours and then cooled to 5° C. The cold reaction mixture was acidified with 6 n hydrogen chloride (640 ml) and extracted with ethyl acetate. The organic layer was washed with 1 N hydrogen chloride (860 ml), water (2×860 ml), saturated aqueous sodium bicarbonate solution (2×860 ml), and brine (860 ml). The organic solution was dried (magnesium sulfate), filtered, and concentrated (room temperature/20 mm Hg). The remaining liquid was distilled to afford the desired product as a yellow oil (259.32 g, 84%). bp.: 70-75° C./0.6 mm Hg; MS m/z: 199 (M+H)+.

1. additionAt the end of the addition
2. washthe addition funnel was rinsed with dichloromethane (80 ml)
3. temperatureto warm to room temperature
4. waitAfter 15 hours at room temperature
5. temperaturethe reaction solution was heated
6. temperatureto reflux for 6 hours
7. temperaturecooled to 5° C
8. customThe cold reaction mixture
9. extractionextracted with ethyl acetate
10. washThe organic layer was washed with 1 N hydrogen chloride (860 ml), water (2×860 ml), saturated aqueous sodium bicarbonate solution (2×860 ml), and brine (860 ml)
11. dry with materialThe organic solution was dried (magnesium sulfate)
12. filtrationfiltered
13. concentrationconcentrated (room temperature/20 mm Hg)
14. distillationThe remaining liquid was distilled

ORD record

ord-417332d5a4b842a2834667a0b700c34d

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06759420B1