N-bromobutanimide → HCID 68979485, compound

HRID 2035419Notes

Reaction equation

HRID 2035419 reaction equation
[CH3:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][NH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.C1C(=O)N([Br:24])C(=O)C1>CC(C)=O>[Br:24][C:15]1[CH:14]=[CH:13][C:4]2[NH:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH:2]([CH3:1])[C:3]=2[CH:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12290108HCID 12290108, compound

Product 1

HCID 68979485HCID 68979485, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 6,11-dihydro-11-methyl-5H-dibenzo[b,e]azepine (4) (8 g, 38.3 mmol) in aceton (1500 mL) was cooled to 0° C. and NBS (N-bromosuccinamide; 6.81 g, 38.3 mmol) was added. The reaction mixture was stirred for 20 min at 0° C., quenched by addition of aqueous NaHCO3 (300 mL) and concentrated under reduced pressure. The product was extracted into ethyl acetate which was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica (Heptane:Ethyl acetate=8:2) to give 2-bromo-6,11-dihydro-11-methyl-5H-dibenzo[b,e]azepine (4, R8═Br; 32 g, 97%) Data: (m/z)=288/290 (M+H)+.

Workup

  1. customquenched by addition of aqueous NaHCO3 (300 mL)
  2. concentrationconcentrated under reduced pressure
  3. extractionThe product was extracted into ethyl acetate which
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica (Heptane:Ethyl acetate=8:2)

Sources & evidence

ORD record
ord-7f622871e0fa4b7e843b878b3f6d4dd0
Source dataset
uspto-grants-2013_11
Patent number
US08575152B2

Reaction notes

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