HCID 73855550, compound → HCID 21947422, compound

Temperature

60 °C

A solution of 3,4-dichlorobenzaldehyde O-(3-morpholin-4-yl-propyl)-oxime (0.160 g, 0.5 mmol) in a mixture of dichloromethane (2 ml) and acetic acid (1 ml) was treated with borane-pyridine complex (0.17 ml, 1.36 mmol) and the resulting mixture was heated under reflux (bath temperature 60° C.) for 4 h. The solvent was then evaporated under reduced pressure and the residue was treated with 10% aqueous hydrochloric acid (3 ml). The reaction mixture was then basified with solid sodium carbonate and extracted with ethyl acetate. The organic phase was then washed with brine, dried (anhydrous magnesium sulfate) and concentrated to give 0.150 g (93% yield) of the crude title hydroxylamine as a light yellow oil which was used as such for the acylation step. 1HNMR 400 MHz (C6D6) δ (ppm): 1.66 (2H, m, CH2), 2.22 (2H, t, J=7.1 Hz, NCH2), 2.24 (4H, m, NCH2), 3.56 (2H, s, NCH2), 3.69 (4H, m, OCH2), 3.70 (2H, t, J=6.5 Hz, OCH2), 5.2 (1H, broad, NH), 6.82 (1H, dd, J=1.9 Hz and J=8.5 Hz, aromatic), 7.13 (1H, d, J=8.5 Hz, aromatic), 7.33 (1H, d, J=1.9 Hz, aromatic).

1. additionwas treated with borane-pyridine complex (0.17 ml, 1.36 mmol)
2. temperaturethe resulting mixture was heated
3. customThe solvent was then evaporated under reduced pressure
4. additionthe residue was treated with 10% aqueous hydrochloric acid (3 ml)
5. extractionextracted with ethyl acetate
6. washThe organic phase was then washed with brine
7. dry with materialdried (anhydrous magnesium sulfate)
8. concentrationconcentrated

ORD record

ord-a83d23aabe014e288bd9a15f1135ebcc

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109186B2