Iodoethane → HCID 12527936, compound

HRID 1577006Notes

Reaction equation

HRID 1577006 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][CH:6]3[CH2:11][CH2:12][N:13]([CH2:15][CH2:16][CH2:17][C:18](=[O:26])[C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH2:14][CH:5]3[C:4]=2[CH:3]=1.[CH2:27](I)[CH3:28].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:27]([N:7]1[C:8]2[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=2[CH:5]2[CH2:14][N:13]([CH2:15][CH2:16][CH2:17][C:18](=[O:26])[C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[CH2:12][CH2:11][CH:6]12)[CH3:28]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 3044949HCID 3044949, compound

Product 1

HCID 12527936HCID 12527936, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To methyl ethyl ketone (60 ml) are added 8-methyl-2-[γ-(p-fluorobenzoyl)propyl]-2,3,4,4a,5,9b-hexahydro-1H-pyrido-[4,3-b]indole (6.6 g), ethyl iodide (3.8 g) and potassium carbonate (5.3 g) and the mixture is refluxed with stirring for 20 hours. After cooling, the insoluble materials are filtered off and the filtrate is concentrated. To the resulting residue is added water and the mixture is extracted with benzene. The benzene layer is dried over anhydrous sodium sulfate and distilled to remove benzene. The resulting residue is treated with ethanolic hydrogen chloride in the same manner as described in Example 1 (1) to give the dihydrochloride of the titled compound (5.2 g), m.p. 150° - 153°C (recrystallized from ethanol).

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling
  3. filtrationthe insoluble materials are filtered off
  4. concentrationthe filtrate is concentrated
  5. additionTo the resulting residue is added water
  6. extractionthe mixture is extracted with benzene
  7. dry with materialThe benzene layer is dried over anhydrous sodium sulfate
  8. distillationdistilled
  9. customto remove benzene
  10. additionThe resulting residue is treated with ethanolic hydrogen chloride in the same manner
  11. customto give
  12. customthe dihydrochloride of the titled compound (5.2 g), m.p. 150° - 153°C (recrystallized from ethanol)

Sources & evidence

ORD record
ord-2ceaca50241d4486994dfec3548a3004
Source dataset
uspto-grants-1976_09
Patent number
US03983239

Reaction notes

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