Morpholine → [2-(Morpholin-4-yl)phenyl]methanol

Temperature

80 °C

2-Fluorobenzaldehyde (1.0 g, 8.1 mmol) was dissolved in DMF (20 mL), morpholine (2.0 mL) and potassium carbonate (1.1 g, 8.1 mmol) were added thereto, and then the mixture was stirred at 80° C. for 2 days. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=98:2 to 60:40) to give an oily matter. The resulting oily matter was dissolved in methanol (20 mL), sodium borohydride (613 mg, 16.2 mmol) was added thereto, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure to give the title compound (474 mg, yield 30%).

1. extractionthe reaction mixture was extracted with ethyl acetate
2. customThe extract was dried
3. concentrationconcentrated under reduced pressure
4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=98:2 to 60:40)
5. customto give an oily matter
6. stirringthe mixture was stirred at room temperature for 3 hours
7. extractionthe reaction mixture was extracted with ethyl acetate
8. customThe extract was dried
9. concentrationconcentrated under reduced pressure

ORD record

ord-7a1371fc483e4f009993f81201af17eb

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008525B2