Sodium Iodide → HCID 13656548, compound

HRID 579750Notes

Reaction equation

HRID 579750 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[CH:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)=[O:6].[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:23][C:24]1[CH:25]=[CH:26][C:27]([N:30]2[CH2:35][CH2:34][N:33]([CH2:2][CH2:3][CH2:4][C:5]([NH:7][CH:8]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[CH:12]=[CH:11][C:10]4[CH:19]=[CH:20][CH:21]=[CH:22][C:9]3=4)=[O:6])[CH2:32][CH2:31]2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 752601-(4-Fluorophenyl)piperazineHCID 13656612HCID 13656612, compound

Product 1

HCID 13656548HCID 13656548, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5.0 g of 5-(4-chlorobutyrylamino)-5H-dibenzo[a,d]cycloheptene, 5.8 g of 1-(4-fluorophenyl)piperazine, 5.0 g of sodium iodide and 50 ml of dimethylformamide is stirred at 100° C. for 1.5 hours. After the reaction mixture is cooled to room temperature, 100 ml of 10% aqueous potassium carbonate solution is added and the solution is extracted with three 300-ml portions of chloroform. The combined extracts are washed successively with water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate, and the chloroform is distilled off. The residue is chromatographed on silica gel with chloroform-methanol (100:3) to give 5.4 g of the title compound. m.p. 233°-235° C. (recrystallized from chloroform-ethyl acetate);

Workup

  1. temperatureAfter the reaction mixture is cooled to room temperature
  2. extractionthe solution is extracted with three 300-ml portions of chloroform
  3. washThe combined extracts are washed successively with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. distillationthe chloroform is distilled off
  6. customThe residue is chromatographed on silica gel with chloroform-methanol (100:3)

Sources & evidence

ORD record
ord-d5a6d93355ff47eea5691d20436126c7
Source dataset
uspto-grants-1988_06
Patent number
US04749703

Reaction notes

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