Morpholine → 4-Phenylmorpholine

Temperature

100 °C

To a toluene solution (3 ml) containing iodobenzene (110 mg), morpholine (73.2 mg), and tert-butoxypotassium (110 mg) the mesh catalyst precursor (12 mm by 14 mm, wire diameter of 0.1 mm, opening of 0.154 mm) prepared in Example 3 was added to be heated for 24 hours at 100° C. The reaction mixture was cooled to room temperature, and the mesh catalyst precursor was washed with ethanol to be taken off from the mixture. The solvent was distilled away from the reaction mixture under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=9:1) to give an intended product, 4-phenylmorpholine with 62% yield. The mesh catalyst precursor taken off from the mixture was recycled in the same reaction to give the intended product, 4-phenyl-morpholine with respective yields of 61%, 57%, 58%, 54%, 58%, 58%, 53%, 53%, 53% from the second to the tenth reaction.

1. customprepared in Example 3
2. additionwas added
3. temperatureThe reaction mixture was cooled to room temperature
4. washthe mesh catalyst precursor was washed with ethanol
5. distillationThe solvent was distilled away from the reaction mixture under reduced pressure
6. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=9:1)

ORD record

ord-433a89b920dd42e3a731294a5eef591a

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09175004B2