Sodium Iodide → HCID 10390243, compound

HRID 37199Notes

Reaction equation

HRID 37199 reaction equation
[C:1]([C:3]1[O:4][C:5]2[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17]Cl)[CH:11]=[CH:10][C:6]=2[C:7](=[O:9])[CH:8]=1)#[N:2].[C:19]1([C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:3]1[O:4][C:5]2[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][N:29]3[CH2:30][CH2:31][C:26](=[C:25]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:27][CH2:28]3)[CH:11]=[CH:10][C:6]=2[C:7](=[O:9])[CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27625334-(Diphenylmethylene)piperidineHCID 104228832-cyano-7-(3-chloropropyloxy)-4-oxo-4H-1-benzopyran

Product 1

HCID 10390243HCID 10390243, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.4 g (1.5 mmol) 2-cyano-7-(3-chloropropyloxy)-4-oxo-4H-1-benzopyran, 0.38 g (1.5 mmol) 4-diphenylmethylenepiperidine, 0.225 g (1.5 mmol) sodium iodide and 0.21 g (1.5 mmol) potassium carbonate in 200 ml dry acetone was refluxed for 48 hours. After removing the solvent, the solid residue was extracted with chloroform. The chloroform solution was evaporated to dryness and the residue was put on a silica gel column and eluated with a mixture of diethylether/ethyl acetate(5:1). Removing the solvents of the collected fractions (Rf=0.39) afforded the compound (6), 2-cyano-7-[3-(4-diphenylmethylenepiperidin-1-yl)propyloxy]-4-oxo-4H-benzopyran as a thick colorless oil (yield: 79%).

Workup

  1. temperaturewas refluxed for 48 hours
  2. customAfter removing the solvent
  3. extractionthe solid residue was extracted with chloroform
  4. customThe chloroform solution was evaporated to dryness
  5. additioneluated with a mixture of diethylether/ethyl acetate(5:1)
  6. customRemoving the solvents of the collected fractions (Rf=0.39)

Sources & evidence

ORD record
ord-f23bfb6b2565480fb9eddf0cc05e6136
Source dataset
uspto-grants-1995_05
Patent number
US05420143

Reaction notes

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