Morpholine → HCID 58021994, compound

To a suspension of 4-chloro-3-nitrobenzaldehyde (1 g) and benzyltriphenylphosphonium bromide (2.34 g) in toluene (35 mL) was added sodium hydride (55%, 0.28 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 1 mol/L hydrochloric acid, and the resulting mixture was extracted with methylene chloride. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=10/1) to give 2-chloro-5-((Z)-2-phenylvinyl)-1-nitrobenzene (0.79 g). The obtained 2-chloro-5-((Z)-2-phenyl -vinyl)-1-nitrobenzene (0.16 g) was dissolved in ethanol (6 mL) -methanol (2 mL). To the solution was added 5% rhodium-carbon powder (20 mg) and morpholine (5 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere overnight. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1) to give the title compound (87 mg).

1. customThe insoluble material was removed by filtration
2. concentrationthe filtrate was concentrated under reduced pressure
3. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1)

ORD record

ord-8e4574515c5041eda09dc121c2eba084

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040693B2