Sodium Iodide → N-[4-(4-diphenylmethyl-1-piperazinyl)-2-butenyl]phthalimide

HRID 868363Notes

Reaction equation

HRID 868363 reaction equation
Br[CH2:2][CH:3]=[CH:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].[C:17]1([CH:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[C:30]1([CH:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:24]2[CH2:25][CH2:26][N:27]([CH2:2][CH:3]=[CH:4][CH2:5][N:6]3[C:10](=[O:11])[C:9]4=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]4[C:7]3=[O:16])[CH2:28][CH2:29]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 534234322-(4-Bromobut-2-en-1-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 53632905N-[4-(4-diphenylmethyl-1-piperazinyl)-2-butenyl]phthalimideYield 50.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.0 g of N-(4-bromo-2-butenyl)phthalimide [cf. Chem. Ber., 93, 2282 (1960)], 5.0 g of 1-diphenylmethylpiperazine, 3.0 g of potassium carbonate, 3.0 g of sodium iodide, and 100 ml of dimethylformamide is stirred at room temperature for 20 hours. After removal of the dimethylformamide by distillation under reduced pressure below 50° C., 50 ml of water is added, and the aqueous mixture is extracted with three 50-ml portions of chloroform. The combined extracts are washed with water, dried over magnesium sulfate, and concentrated. The residue is chromatographed on silica gel with toluene to give 4.1 g of N-[4-(4-diphenylmethyl-1-piperazinyl)-2-butenyl]phthalimide.

Workup

  1. customAfter removal of the dimethylformamide
  2. distillationby distillation under reduced pressure below 50° C., 50 ml of water
  3. additionis added
  4. extractionthe aqueous mixture is extracted with three 50-ml portions of chloroform
  5. washThe combined extracts are washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel with toluene

Sources & evidence

ORD record
ord-12c0203e956a4d6486089e55e7277478
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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