3-(4-Pentylphenyl)propyl mesylate → N-3-(4-pentylphenyl)propylphthalimide

HRID 1072715Notes

Reaction equation

HRID 1072715 reaction equation
S(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=1)(=O)(=O)C.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[K]>CN(C=O)C>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][N:24]2[C:23](=[O:25])[C:22]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]3[C:20]2=[O:30])=[CH:10][CH:11]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 223874783-(4-Pentylphenyl)propyl mesylateHCID 24194345Phthalimide potassium salt

Product 1

HCID 22387439N-3-(4-pentylphenyl)propylphthalimideYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-pentylphenyl)propyl mesylate (42.4 g, 149 mmol) and potassium phthalimide (27.6 g, 149 mmol) in DMF (200 ml) was stirred at 80° C. for 3 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate anhydride, and the organic layer was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the object compound as an oily substance. 41.1 g, (yield 82%)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate anhydride
  4. concentrationthe organic layer was concentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)
  6. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-8772f1f9ebbc47c2a3791876ec8b35c7
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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