Nitric Acid → HCID 565523, compound

Temperature

0 °C

To a vigorously stirred mixture of concentrated sulfuric acid (22.7 mL) and 65% nitric acid (2.3 mL) at 0° C. was added C-adamantan-1-yl-methylamine (2.0 g, 12.12 mmol) dropwise. The reaction mixture was stirred for 2 h at 0° C., warmed to room temperature and stirred at that temperature for 24 h, cooled to 0° C. and slowly quenched with ice (10.8 g). The mixture was allowed to warm to ambient as ice melts overnight, cooled to 0° C. again and treated with sodium hydroxide (50 g) in small portions. The resulting brownish paste was filtered, and the filter cake was rinsed with DCM (200 mL). After separation, the organic layer was washed with brine (2×20 mL), dried over sodium sulfate, filtered and concentrated to give a white solid (1.09 g). (m/z): [M+H]+ calcd for C11H19N, 182.2. found 182.2.

1. temperaturewarmed to room temperature
2. stirringstirred at that temperature for 24 h
3. temperaturecooled to 0° C.
4. customslowly quenched with ice (10.8 g)
5. temperatureto warm to ambient as ice
6. waitmelts overnight
7. temperaturecooled to 0° C. again
8. additiontreated with sodium hydroxide (50 g) in small portions
9. filtrationThe resulting brownish paste was filtered
10. washthe filter cake was rinsed with DCM (200 mL)
11. customAfter separation
12. washthe organic layer was washed with brine (2×20 mL)
13. dry with materialdried over sodium sulfate
14. filtrationfiltered
15. concentrationconcentrated

ORD record

ord-2ef7456edb0e4cedbfe2c379056c071a

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206172B2