Sodium Iodide → HCID 18962976, compound

HRID 1707286Notes

Reaction equation

HRID 1707286 reaction equation
[C:1]([C:4]1[CH:5]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:6]([C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16]Cl)=[C:7]([CH3:11])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].[C:28]1([C:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[C:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[C:1]([C:4]1[CH:5]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:6]([C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][N:38]2[CH2:39][CH2:40][C:35](=[C:34]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:36][CH2:37]2)=[C:7]([CH3:11])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 27625334-(Diphenylmethylene)piperidineHCID 18962985HCID 18962985, compound

Product 1

HCID 18962976HCID 18962976, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4.7 g (12 mmol) 5-acetyl-1,4-dihydro-2,6-dimethyl-3-(5-chloropentanoyl)-4-(3-nitrophenyl)-pyridine and 3 g (14 mmol) 4-diphenylmethylenepiperidine are boiled under reflux with 1.9 g (12 mmol) sodium iodide and 5 g (48 mmol) sodium carbonate in 200 ml acetone for 5 days. The mixture is filtered and concentrated, and the residue is taken up in 100 ml ethyl acetate. This solution is extracted by shaking with 40 ml sodium thiosulphate solution (5%). The organic phase is dried over magnesium sulphate, filtered and concentrated. The residue is chromatographed with toluene/acetone=6/4, The title compound is obtained as a yellow oil. Yield: 2.2 g (32%).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated
  3. extractionThis solution is extracted
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is chromatographed with toluene/acetone=6/4

Sources & evidence

ORD record
ord-3ea064da50bb4f1eb6ca3642a8ddf1df
Source dataset
uspto-grants-1994_10
Patent number
US05352684

Reaction notes

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