HCID 16228101, compound → HCID 22605500, compound

Lithium aluminum hydride (2.28 g, 60 mmol) was carefully added to a suspension of (±)-6-(1-aminoethyl)-4H-benzo[1,4]oxazin-3-one, Preparation 11 (3.84 g, 20 mmol) in THF (80 mL) at −78° C. The reaction mixture was stirred while warming to room temperature, then under reflux for 4 hours. The reaction mixture was then cooled to −78° C. and was quenched with water (2.3 mL), sodium hydroxide (10N) (2.3 mL), and water (4.6 mL). The resulting mixture was filtered and the resultant filtrate was concentrated in vacuo. The residual material was extracted with CH2Cl2 (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered and the resultant filtrate was concentrated in vacuo to provide the title compound (3.38 g, 95%) as an oil.

1. temperatureunder reflux for 4 hours
2. temperatureThe reaction mixture was then cooled to −78° C.
3. customwas quenched with water (2.3 mL), sodium hydroxide (10N) (2.3 mL), and water (4.6 mL)
4. filtrationThe resulting mixture was filtered
5. concentrationthe resultant filtrate was concentrated in vacuo
6. extractionThe residual material was extracted with CH2Cl2 (3×50 mL)
7. dry with materialThe combined organic layers were dried over sodium sulfate
8. filtrationfiltered
9. concentrationthe resultant filtrate was concentrated in vacuo

ORD record

ord-d7b9e9f0b3b34baa8e39a7e7deb90f13

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06831080B2