Sodium Iodide → HCID 18962987, compound

HRID 1707273Notes

Reaction equation

HRID 1707273 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:17])=[C:7]([CH3:11])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].[I-].[Na+].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.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O1CCOCC1.C(O)(C)C.C(OCC)C>[ClH:17].[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:40]2[CH2:41][CH2:42][C:37]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:38][CH2:39]2)=[C:7]([CH3:11])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 30475044,4-Diphenylpiperidine hydrochlorideHCID 18962985HCID 18962985, compound

Product 1

HCID 18962987HCID 18962987, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Procedure

5.5 g (14 mmol) 5-acetyl-1,4-dihydro-2,6-dimethyl-3-(5-chloropentanoyl)-4-(3-nitrophenyl)-pyridine and 4.2 g (28 mmol) sodium iodide are boiled under reflux in 200 ml anhydrous acetone for 24 h. The mixture is filtered and concentrated. The residue is boiled under reflux together with 8 g (28 mmol) 4,4-diphenylpiperidine hydrochloride and 8 g (58 mmol) potassium carbonate in 100 ml dioxane for 24 h. The mixture is filtered and concentrated, and the residue is chromatographed over silica gel with toluene/acetone=2/8. The product thus obtained is taken up in 120 ml isopropanol and the mixture is diluted with 150 ml diethyl ether. The title compound is precipitated by addition of ethereal hydrochloric acid . Yield: 4.75 g (54%). M.p.: 164°-167° C. (acetonitrile).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated
  5. customthe residue is chromatographed over silica gel with toluene/acetone=2/8
  6. customThe product thus obtained
  7. customThe title compound is precipitated by addition of ethereal hydrochloric acid

Sources & evidence

ORD record
ord-082b368bbcd646269af5a9e10eb2cbb6
Source dataset
uspto-grants-1994_10
Patent number
US05352684

Reaction notes

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