Potassium Iodide → HCID 20222394, compound

HRID 1414037Notes

Reaction equation

HRID 1414037 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13]Cl.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.[K].[I-].[K+]>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][N:19]1[C:15](=[O:25])[C:16]2[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:18]1=[O:20]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 20289483HCID 20289483, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 20222394HCID 20222394, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 5-bromo-3-(3-chloropropyl)-1H-indole (1.35 g), potassium phthalimide (0.93 g) and potassium iodide (1.3 g) in dry dimethylformamide (20 ml) was warmed with stirring at 105° C. for 3 hours. The mixture was cooled and diluted with water (30 ml). An oil precipitated which crystallised over the next 5 min. The resulting solid was collected and washed thoroughly with water. The product was recrystallised from 2-propanol (50 ml) to afford the title compound as a pale yellow crystalline solid (1.1 g) m.p. 168.5°-170° C.

Workup

  1. temperaturewas warmed
  2. temperatureThe mixture was cooled
  3. customAn oil precipitated which
  4. customcrystallised over the next 5 min
  5. customThe resulting solid was collected
  6. washwashed thoroughly with water
  7. customThe product was recrystallised from 2-propanol (50 ml)

Sources & evidence

ORD record
ord-f94361ee5de44f909390e0f940dc83d1
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

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