1,4-Benzodioxan-6-yl methyl ketone → 1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethanamine

A mixture of 1-(2,3-dihydro-1,4-benzodioxin-6-yl)acetaldehyde, oxime, (Preparation 5, 10.74 g, 0.0556 mole), and Raney nickel (1 mL) in ammonium hydroxide/methanol (20 mL/200 mL) was hydrogenated (H2, 50 psi) for 48 hours. The reaction mixture was filtered through Celite and the resultant filtrate was concentrated in vacuo. The residual oil obtained was diluted with HCl (1N). The aqueous layer was washed with EtOAc (1×250 mL). The aqueous layer was then made basic with NaOH (1N), and extracted with EtOAc (3×200 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and the resultant filtrate was concentrated in vacuo to provide the title product (7.1 g, 66%) as a clear oil.

1. customfor 48 hours
2. filtrationThe reaction mixture was filtered through Celite
3. concentrationthe resultant filtrate was concentrated in vacuo
4. customThe residual oil obtained
5. washThe aqueous layer was washed with EtOAc (1×250 mL)
6. extractionextracted with EtOAc (3×200 mL)
7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationthe resultant filtrate was concentrated in vacuo

ORD record

ord-d967f24a6a3a4a9fa0204c971aadbe38

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06831080B2