Triethylamine → HCID 22605519, compound

A mixture of 1-(3-fluoro-5-morpholin-4-yl-phenyl)ethanone (2.23 g), NH2OH.HCl (1.4 g), and Et3N (2.8 mL) in EtOH (20 mL) was refluxed for 3 hours. After concentration, the residue was extracted with CH2Cl2. The organic layer was washed with water, dried over MgSO4 and concentrated in vacuo. A suspension of the resulting residue (2.23 g) and Ra—Ni (1 mL) in a mixture of 3 mL of 30% ammonium hydroxide and 15 mL of MeOH was hydrogenated at 50 psi for 16 hours. The crude reaction mixture was filtered through Celite, and the filtrate was concentrated in vacuo. The crude product was purified by silica gel flash chromatography (10% ammonium hydroxide in methanol) to give 1.665 g of the title compound as an oil.

1. temperaturewas refluxed for 3 hours
2. concentrationAfter concentration
3. extractionthe residue was extracted with CH2Cl2
4. washThe organic layer was washed with water
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. additionA suspension of the resulting residue (2.23 g) and Ra—Ni (1 mL)
8. additionin a mixture of 3 mL of 30% ammonium hydroxide and 15 mL of MeOH
9. customThe crude reaction mixture
10. filtrationwas filtered through Celite
11. concentrationthe filtrate was concentrated in vacuo
12. customThe crude product was purified by silica gel flash chromatography (10% ammonium hydroxide in methanol)

ORD record

ord-5cede81078574e7384ea4707ed6bc2a4

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06831080B2