Hydrochloric Acid → HCID 15647727, compound

To a solution of 1-morpholino-1-cyclohexene (51 g; 300 mmol) in 120 mL anhydrous acetonitrile at 0-4° C. was added the 2-nitroethylacetate product of Example 2a (37.8 g, 293 mmol) dropwise. The resulting red solution was stirred under N2 atmosphere in an ice bath for 2½ hrs. The red solution was then stirred at ambient temperature under an N2 atmosphere overnight. Water (100 mL) was added to the red solution over a 10-15 minute period. The temperature rose from 20 to 29° C. with the first 200 mL of water, but then dropped to 27° C. by the end of the addition. This was then acidified with aqueous HCl. The dark red reaction mixture was diluted with 85 mL of EtOAc and the layers separated. The light orange water layer (bottom) was extracted again with 50 mL of EtOAc. The combined EtOAc layers were washed with saturated brine (2×85 mL), dried (MgSO4), filtered and concentrated to afford 45 g of 2-(2-nitroethyl)cyclohexanone as a red oil.

1. stirringThe red solution was then stirred at ambient temperature under an N2 atmosphere overnight
2. additiondropped to 27° C. by the end of the addition
3. customThe dark red reaction mixture
4. customthe layers separated
5. extractionThe light orange water layer (bottom) was extracted again with 50 mL of EtOAc
6. washThe combined EtOAc layers were washed with saturated brine (2×85 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-0ffe502774bb49b3bafc722baf02f464

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06489323B1