Sodium Iodide → HCID 67937927, compound

HRID 868337Notes

Reaction equation

HRID 868337 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15]Cl)=[O:11])=[CH:4][CH:3]=1.[C:17]1([CH:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(C(C)=O)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][N:27]2[CH2:28][CH2:29][N:24]([CH:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:25][CH2:26]2)=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 54007979HCID 54007979, compound

Product 1

HCID 67937927HCID 67937927, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1.0 g of N-[3-(6-methyl-3-pyridyl)acryloyl]-3-amino-1-chloropropane, 1.0 g of 1-diphenylmethylpiperazine, 0.55 g of potassium carbonate, 0.55 g of sodium iodide, and 30 ml of methyl ethyl ketone is refluxed with stirring for 6 hours. The reaction mixture is concentrated, and 20 ml of water is added. The mixture is extracted with three 30-ml portions of chloroform. The combined extracts are dried over magnesium sulfate, and the chloroform is distilled off. The residue is chromatographed on silica gel with chloroform-methanol (30:1) to give 0.65 g of the title compound. The product is converted into the fumarate in a usual manner to give the trifumarate 3/4 hydrate of the title compound. m.p. 196°-200° C. (recrystallized from ethanol)

Workup

  1. temperatureis refluxed
  2. concentrationThe reaction mixture is concentrated
  3. addition20 ml of water is added
  4. extractionThe mixture is extracted with three 30-ml portions of chloroform
  5. dry with materialThe combined extracts are dried over magnesium sulfate
  6. distillationthe chloroform is distilled off
  7. customThe residue is chromatographed on silica gel with chloroform-methanol (30:1)

Sources & evidence

ORD record
ord-9db3f4582a214d3c904fff26b428ab66
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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