HCID 68280040, compound → Diphenylamine

Temperature

100 °C

0.01 mmol of the complex 1 produced in Example 1 and 5 mmol of N,N-diphenyloctanamide were placed in a 50 mL-autoclave equipped with a stirrer, and the autoclave was purged with nitrogen. 1.5 mL of methanol and 2.5 mL of methanol solution of 2.0 M sodium methoxide were added to the autoclave, and the autoclave was purged with hydrogen. The resulting mixture was stirred under hydrogen atmosphere (5 MPa) and 100 degrees C. for 16 hours to obtain a reaction solution. After the completion of reaction, the reaction solution was cooled, diluted with 40 mL of dichloromethane, and subjected to silica gel filtration (eluting solvent: dichloromethane/methanol=10/1). The thus obtained solution was concentrated, and then the resulting residue was purified by silica gel column chromatography (silica gel: 40 g, hexane/ethyl acetate=8/1 to 4/1). As a result, 1-octanol (500 mg, 77%) and N,N-diphenylamine (800 mg, 95%) were obtained.

1. customequipped with a stirrer
2. customthe autoclave was purged with nitrogen
3. addition1.5 mL of methanol and 2.5 mL of methanol solution of 2.0 M sodium methoxide were added to the autoclave
4. customthe autoclave was purged with hydrogen
5. customfor 16 hours to obtain a reaction solution
6. customAfter the completion of reaction
7. temperaturethe reaction solution was cooled
8. filtrationsubjected to silica gel filtration (eluting solvent: dichloromethane/methanol=10/1)
9. concentrationThe thus obtained solution was concentrated
10. customthe resulting residue was purified by silica gel column chromatography (silica gel: 40 g, hexane/ethyl acetate=8/1 to 4/1)

ORD record

ord-a4bc44cb9bd04174ac39b41208653d9c

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012690B2