Ethyl 1-cyanocyclohexane-1-carboxylate → Ethyl 1-[(benzoylamino)methyl]cyclohexanecarboxylate

A solution of ethyl 1-cyanocyclohexanecarboxylate (10.0 g, 55.1 mmol) in ethanol (200 ml) was stirred at 40° C. for 12 hrs., in the presence of Raney-nickel (10 g), under a hydrogen atmosphere (4 atm). The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. Ethyl acetate (300 ml) and 10% aqueous sodium carbonate solution (150 ml) were added to the residue, benzoyl chloride (6.34 ml, 55.1 ml) was added dropwise at 0° C., and the mixture was stirred at room temperature for 6 hrs. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous MgSO4. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (3:1-1:1, v/v) to give the title compound (10.2 g, 63%) as a colorless oil.

1. filtrationThe catalyst was filtered off
2. concentrationthe filtrate was concentrated under reduced pressure
3. additionEthyl acetate (300 ml) and 10% aqueous sodium carbonate solution (150 ml) were added to the residue, benzoyl chloride (6.34 ml, 55.1 ml)
4. additionwas added dropwise at 0° C.
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with ethyl acetate
7. dry with materialdried over anhydrous MgSO4
8. concentrationAfter concentration under reduced pressure
9. washeluted with hexane-ethyl acetate (3:1-1:1

ORD record

ord-86251d10e2314136949d7cceef09de3a

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07973163B2