Water → HCID 15628568, compound

HRID 434705Notes

Reaction equation

HRID 434705 reaction equation
[CH3:1][C:2]12[C:13]3[CH:14]=[C:15](Br)[CH:16]=[CH:17][C:12]=3[CH2:11][CH:9]([NH:10]1)[C:8]1[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].CN([CH:25]=[O:26])C.O>[Cu].CCOCC>[CH3:1][C:2]12[C:13]3[CH:14]=[C:15]([O:26][CH3:25])[CH:16]=[CH:17][C:12]=3[CH2:11][CH:9]([NH:10]1)[C:8]1[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 13194161HCID 13194161, compound

Product 1

HCID 15628568HCID 15628568, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.00905 mol of 3-bromo-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine, 0.181 mol of sodium methoxide, 5.56 g of electrolytic copper dust, and 87 ml of DMF is stirred and heated on a steam bath for 2.5 hours. After cooling, 150 ml of water and 150 ml of ether is added to the mixture, and, after stirring, the mixture is filtered through a pad of celite. The ether phase is separated, washed with water, dried over magnesium sulfate, filtered, and the ether is removed on a rotary evaporator. The residue is dissolved in warm acetonitrile. On standing, the solution deposits crystals. The supernatant, containing the desired product, is decanted from the crystals. Evaporation of the solvent gives 3-methoxy-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine.

Workup

  1. temperatureheated on a steam bath for 2.5 hours
  2. temperatureAfter cooling
  3. stirringafter stirring
  4. filtrationthe mixture is filtered through a pad of celite
  5. customThe ether phase is separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe ether is removed on a rotary evaporator
  10. dissolutionThe residue is dissolved in warm acetonitrile
  11. additionThe supernatant, containing the desired product
  12. customis decanted from the crystals
  13. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e9b26d8dfdce4d478d24a5dd3574b93d
Source dataset
uspto-grants-1983_08
Patent number
US04399141

Reaction notes

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