Cyanogen Bromide → HCID 13055166, compound

HRID 1388887Notes

Reaction equation

HRID 1388887 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][N:23](C)[CH3:24])([C:8](=O)C2C=CC=CC=2)N[CH:7]=1.[N:26]#[C:27]Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:22][N:23]=[C:24]([C:4]3[CH:3]=[CH:2][CH:7]=[CH:27][N:26]=3)[C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 20468885HCID 20468885, compound

Product 1

HCID 13055166HCID 13055166, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The solution of 4.5 g of 5-chloro-2-(o-dimethylaminomethyl-phenyl)-2-benzoylpyridine in 120 ml of methylene chloride is treated during 4 hours with 13.7 ml of 0.94 molar cyanogen bromide in methylene chloride. The mixture is evaporated, the residue dissolved in 200 ml of saturated methanolic ammonia, and the solution evaporated after 2 days. The residue is taken up in aqueous sodium carbonate, the mixture extracted with diethyl ether, the extract washed with saturated aqueous sodium chloride, decolorized with activated charcoal, evaporated and the residue crystallized from diethyl ether to give the 9-chloro-7-(2-pyridyl)-5H-dibenz[c,e]azepine melting at 153°-155°.

Workup

  1. customThe mixture is evaporated
  2. dissolutionthe residue dissolved in 200 ml of saturated methanolic ammonia
  3. customthe solution evaporated after 2 days
  4. extractionthe mixture extracted with diethyl ether
  5. washthe extract washed with saturated aqueous sodium chloride
  6. customevaporated
  7. customthe residue crystallized from diethyl ether

Sources & evidence

ORD record
ord-d989782e04f3494fa99f23b0d2919372
Source dataset
uspto-grants-1984_02
Patent number
US04434100

Reaction notes

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