8-Chloro-10,11-dihydro-5H-dibenzo[b,f][1,4]diazepine → HCID 136085037, compound

To a solution of 8-chloro-10,11-dihydro-5H-dibenzo[b,f][1,4]diazepine (8.75 g, 37.9 mmol) in CH2Cl2 (375 mL) was added MnO2 (14.5 g, 166 mmol). The reaction mixture was stirred at room temperature for 1.5 h. After filtration through dicalite, washing with CH2Cl2, the volatiles were removed in vacuo. The crude product was dissolved in ethanol (250 mL) wherafter 2N (aq) NaOH (20 mL) was added. This mixture was stirred at room temperature for 2.5 h. The reaction mixture was filtrated through dicalite and washed with CH2Cl2. After removal of the solvent under reduced pressure, the residu was dissolved in ethanol (350 mL). NaOH (2N, 20 mL) was added and the mixture was stirred for 3 h. Water was added and the mixture was extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried and evaporated to afford the title compound (8.9 g, 38.9 mmol).

1. filtrationAfter filtration through dicalite
2. washwashing with CH2Cl2
3. customthe volatiles were removed in vacuo
4. dissolutionThe crude product was dissolved in ethanol (250 mL) wherafter 2N (aq) NaOH (20 mL)
5. additionwas added
6. stirringThis mixture was stirred at room temperature for 2.5 h
7. filtrationThe reaction mixture was filtrated through dicalite
8. washwashed with CH2Cl2
9. customAfter removal of the solvent under reduced pressure
10. dissolutionthe residu was dissolved in ethanol (350 mL)
11. additionNaOH (2N, 20 mL) was added
12. stirringthe mixture was stirred for 3 h
13. additionWater was added
14. extractionthe mixture was extracted with ethyl acetate (3×)
15. washThe combined organic layers were washed with brine
16. customdried
17. customevaporated

ORD record

ord-bac32aa16a0143ae82d270190b816ba0

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07737136B2