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-[(8-chloro-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 room temperature 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), CH2C2 (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 CH2C2. 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 room temperature
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. temperatureCH2C2 (5 mL), and conc. HCl (3 mL) and heated at 60° C. for 1 h
8. custompartitioned between water and CH2C2
9. washThe organic layer is washed with water
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated

ORD record

ord-fc33192e4b144d2993c17992e02f4b0a

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06448397B1