Water → HCID 58046603, compound

HRID 236873Notes

Reaction equation

HRID 236873 reaction equation
[Na].[I-].[CH3:3][N+:4]1[CH:9]=[CH:8][C:7]2[C:10]3[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=3[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:6]=2[CH:5]=1.O>C(O)C>[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]2[C:10]3[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=3[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH:6]2[CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 5360545SodiumHCID 70572305HCID 70572305, compound2×

Product 1

HCID 58046603HCID 58046603, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4 g Sodium is added with stirring and under a nitrogen atmosphere to a suspension of 0.5 g 2-methyl-9H-dibenzo[1,2;5,6]cyclohepta[3,4-c]pyridinium iodide (formula IV, melting point >300° C.) in 50 ml ethanol, after which the mixture is refluxed for 1 hour. The reaction mixture is then poured out into H2O and extracted with methylene chloride. The organic phase is washed with H2O, dried over Na2SO4 and evaporated to dryness. Yield: 260 mg (76%) of a mixture of cis- and trans-2-methyl-2,3,4,4a,9,13b-hexahydro-1H-dibenzo[1,2;5,6] cyclohepta[3,4-c]pyridine. Rf in toluene:ethanol (7:3)=0.27 for the trans-compound and 0.65 for the cis-compound.

Workup

  1. temperatureafter which the mixture is refluxed for 1 hour
  2. extractionextracted with methylene chloride
  3. washThe organic phase is washed with H2O
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-92b828e34d2c4787b23430d2b97fc97d
Source dataset
uspto-grants-1979_06
Patent number
US04158058

Reaction notes

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