1-Bromo-3-chloropropane → HCID 22102513, compound

HRID 1456927Notes

Reaction equation

HRID 1456927 reaction equation
[CH:1]1[C:11]2[C:10](=[O:12])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=[O:17])[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:21][CH2:22][CH2:23][Cl:24].[Cl-].[NH4+]>CN(C)C=O>[Cl:24][CH2:23][CH2:22][CH2:21][N:6]1[C:7](=[O:17])[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](=[O:12])[C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

6

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 708365H-Dibenz(b,e)azepine-6,11-dione

Product 1

HCID 22102513HCID 22102513, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5H-dibenz[b,e]azepine-6,11-dione (3.0 g, 0.013 mol) in dry N,N-dimethylformamide (25 ml) kept under an atmosphere of nitrogen, sodium hydride (0.7 g, 0.027 mol, 60% dispersion in mineral oil) was added in portions and the reaction mixture was stirred for 1.5 hour. 1-Bromo-3-chloropropane (5.0 g, 0.031 mol) dissolved in N,N-dimethylformamide was slowly added and the mixture was stirred overnight. Ammonium chloride (2.0 g, 0.04 mol) was added and stirring was continued for 30 minutes. The solution was poured onto water (300 ml) and the mixture was extracted with dichloromethane (2×200 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel (150 g) using a mixture of heptane and ethyl acetate (4:1) as eluent to give 3.1 g (79%) of 5-(3-chloropropyl)-5H-dibenz[b,e]azepine-6,11-dione as an oil.

Workup

  1. additionwas slowly added
  2. stirringthe mixture was stirred overnight
  3. stirringstirring
  4. waitwas continued for 30 minutes
  5. additionThe solution was poured onto water (300 ml)
  6. extractionthe mixture was extracted with dichloromethane (2×200 ml)
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated in vacuo
  10. customThe residue was purified by column chromatography on silica gel (150 g)
  11. additiona mixture of heptane and ethyl acetate (4:1) as eluent

Sources & evidence

ORD record
ord-f3b3c8eedff94517ad6ac5a885c4902c
Source dataset
uspto-grants-1998_12
Patent number
US05846968

Reaction notes

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