Methanol → 2-[(8-Chloro-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]-1-ethanamine

Temperature

82 °C

To a mixture of 2-[(8chloro-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]acetonitrile (0.2838 g, 0.757 mmol) in dry THF (10 mL) is added borane-methylsulfide complex (0.22 mL, 2.27 mmol). The mixture is refluxed under an argon atmosphere at 82° C. for 18 h. The mixture is then cooled, to rt and methanol is slowly added until gas evolution ceased. The solvents are removed under vacuum and methanol (5 mL) is added and again removed. The residue is dissolved in methanol (10 mL), CH2Cl2 (5 mL), and conc. HCl (3 mL) and heated at 60° C. for 1 h. The mixture is neutralized with aqueous potassium carbonate and partitioned between water and CH2Cl2. The organic layer is washed with water, dried over magnesium sulfate and concentrated. Column chromatography (50 g silica gel) using CH3OH/CH2Cl2 (4/96) as eluent gave 0.080g (28%) of 2-[(8-chloro-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]-1-ethanamine; mp 127-128° C.

1. additionis added borane-methylsulfide complex (0.22 mL, 2.27 mmol)
2. temperatureThe mixture is then cooled, to rt
3. customThe solvents are removed under vacuum and methanol (5 mL)
4. additionis added
5. customagain removed
6. dissolutionThe residue is dissolved in methanol (10 mL)
7. temperatureCH2Cl2 (5 mL), and conc. HCl (3 mL) and heated at 60° C. for 1 h
8. custompartitioned between water and CH2Cl2
9. washThe organic layer is washed with water
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated

ORD record

ord-e7ac2a255f964916bd6ba0a71c6eff1d

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06932961B1