Sodium Iodide → N-[4-(4-diphenylmethylene-1-piperidyl)butyl]phthalimide

HRID 1089124Notes

Reaction equation

HRID 1089124 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[CH2:9][CH2:10][N:11]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]3[C:29](=[O:30])[C:28]4=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]4[C:26]3=[O:35])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 27625334-(Diphenylmethylene)piperidine

Product 1

HCID 15096000N-[4-(4-diphenylmethylene-1-piperidyl)butyl]phthalimideYield 79.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-Diphenylmethylenepiperidine (9.5 g), N-(4-bromobutyl)phthalimide (16 g), sodium iodide (8 g) and potassium carbonate (9 g) are added to methyl ethyl ketone (200 ml) and the mixture is refluxed with stirring for 4 hours. The reaction mixture is concentrated and water (150 ml) is added to the residue. The aqueous layer is extracted three times with chloroform (each 100 ml). The combined extracts are dried over anhydrous magnesium sulfate and then concentrated. The residue is subjected to silica gel column chromatography, followed by elution with chloroform to give N-[4-(4-diphenylmethylene-1-piperidyl)butyl]phthalimide (13.7 g).

Workup

  1. temperaturethe mixture is refluxed
  2. concentrationThe reaction mixture is concentrated
  3. additionwater (150 ml) is added to the residue
  4. extractionThe aqueous layer is extracted three times with chloroform (each 100 ml)
  5. dry with materialThe combined extracts are dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. washfollowed by elution with chloroform

Sources & evidence

ORD record
ord-05a957e1c71c4736ae1971eb6f91d9ee
Source dataset
uspto-grants-1990_10
Patent number
US04965266

Reaction notes

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