HCID 68979485, compound → HCID 68976360, compound

HRID 2035420Notes

Reaction equation

HRID 2035420 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]([CH3:11])[C:4]=2[CH:3]=1>C(Cl)Cl.O=[Mn]=O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]([CH3:11])[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 68979485HCID 68979485, compound

Product 1

HCID 68976360HCID 68976360, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-6,11-dihydro-11-methyl -5H-dibenzo[b,e]azepine (4, R8=Br; 32 g, 0.11 mol) in DCM, MnO2 (manganese oxide)(96.6 g, 1.11 mol) was added and the reaction mixture was allowed to stir overnight. The reaction mixture was filtered over decalite and concentrated under reduced pressure. The crude product was purified by column chromatography on silica (Heptane:Ethyl acetate=8:2) to give 2-bromo-11-methyl-11H-dibenzo[b,e]azepine (5, R8═Br; 29.4 g, 92%). Data: (m/z)=286/288 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered over decalite
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by column chromatography on silica (Heptane:Ethyl acetate=8:2)

Sources & evidence

ORD record
ord-e0663ccaea3d442aa7d960bdf41fb86d
Source dataset
uspto-grants-2013_11
Patent number
US08575152B2

Reaction notes

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