Sodium Iodide → HCID 18962957, compound

HRID 1707285Notes

Reaction equation

HRID 1707285 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:17]2[C:16](=[O:28])[CH2:15][CH2:14][CH2:13][C:12]=2[NH:11][C:10]=1[CH3:29])=[O:8].Cl.[C:31]1([C:37]2([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[C:31]1([C:37]2([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:38][CH2:39][N:40]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]3[CH:18]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=4)[C:17]4[C:16](=[O:28])[CH2:15][CH2:14][CH2:13][C:12]=4[NH:11][C:10]=3[CH3:29])=[O:8])[CH2:41][CH2:42]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 30475044,4-Diphenylpiperidine hydrochlorideHCID 67819953HCID 67819953, compound

Product 1

HCID 18962957HCID 18962957, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6.6 g (16 mmol) 3-(6-chlorohexanoyl)-1,4,5,6,7,8,-hexahydro-2-methyl-4-(3-nitrophenyl) 5-oxo-quinoline and 9 g( 32 mmol) 4,4-diphenylpiperidine hydrochloride are boiled under reflux with 2.5 g (16 mmol) sodium iodide and 7 g (66 mmol) sodium carbonate in 150 ml acetone for 6 days. The mixture is filtered and concentrated, and the residue is taken up in 150 ml ethyl acetate. The mixture 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 over silica gel with toluene/acetone=8/2. The title compound is obtained as a yellow oil. Yield: 8 g (82%).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated
  3. extractionThe mixture is extracted
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is chromatographed over silica gel with toluene/acetone=8/2

Sources & evidence

ORD record
ord-976d05d15bef4505b0339b9e9bb0c071
Source dataset
uspto-grants-1994_10
Patent number
US05352684

Reaction notes

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