Potassium Iodide → HCID 12527921, compound

HRID 1577003Notes

Reaction equation

HRID 1577003 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:9]2[NH:8][CH:7]3[CH2:12][CH2:13][NH:14][CH2:15][CH:6]3[C:5]=2[CH:4]=1)[CH3:2].[F:16][C:17]1[CH:28]=[CH:27][C:20]([C:21]([CH2:23][CH2:24][CH2:25]Cl)=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)C>[CH2:1]([C:3]1[CH:11]=[CH:10][C:9]2[NH:8][CH:7]3[CH2:12][CH2:13][N:14]([CH2:25][CH2:24][CH2:23][C:21](=[O:22])[C:20]4[CH:19]=[CH:18][C:17]([F:16])=[CH:28][CH:27]=4)[CH2:15][CH:6]3[C:5]=2[CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 125278768-Ethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 12527921HCID 12527921, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To methyl ethyl ketone (120 ml) are added 8-ethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (9 g), γ-(p-fluorobenzoyl)propyl chloride (12 g), potassium carbonate (12 g) and potassium iodide (11 g), and the mixture is refluxed with stirring for 9 hours. After cooling, the insoluble materials are filtered off and the filtrate is concentrated. The resulting residue is dissolved in a dilute hydrochloric acid and the solution is washed with benzene. The dilute hydrochloric acid layer is made alkaline with aqueous ammonia and extracted with benzene. The benzene layer is dried over anhydrous sodium sulfate and concentrated. The resulting residue is treated with ethanolic hydrochloric acid in the same manner as described in Example 1 (1) to give the dihydrochloride of the titled compound (12 g), m.p. 192° - 195°C (recrystallized from aqueous ethanol).

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling
  3. filtrationthe insoluble materials are filtered off
  4. concentrationthe filtrate is concentrated
  5. dissolutionThe resulting residue is dissolved in a dilute hydrochloric acid
  6. washthe solution is washed with benzene
  7. extractionextracted with benzene
  8. dry with materialThe benzene layer is dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. additionThe resulting residue is treated with ethanolic hydrochloric acid in the same manner
  11. customto give
  12. customthe dihydrochloride of the titled compound (12 g), m.p. 192° - 195°C (recrystallized from aqueous ethanol)

Sources & evidence

ORD record
ord-4c2c3d78dfa249f0b175e1c4d807cc84
Source dataset
uspto-grants-1976_09
Patent number
US03983239

Reaction notes

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