Phthalimide → N-(4-Bromopentyl)phthalimide

HRID 1018031Notes

Reaction equation

HRID 1018031 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][CH2:15][CH2:16][CH:17]([Br:19])[CH3:18].C1(=O)NC(=O)C2=CC=CC=C12>CC(C)=O>[Br:19][CH:17]([CH3:18])[CH2:16][CH2:15][CH2:14][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 79082Pentane, 1,4-dibromo-HCID 24194345Phthalimide potassium salt

Product 1

HCID 240534N-(4-Bromopentyl)phthalimideYield 97.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
15 °C

Procedure

A one liter, four necked round bottom flask equipped with a mechanical stirrer, thermowatch and condenser was charged with acetone (500 ml), potassium phthalimide (92.5 g, 0.5 moles) and 1,4-dibromopentane (153 g, 0.665 moles). The resulting mixture was refluxed for 24 hours (HPLC showed 2.5% unreacted phthalimide), then cooled to 15° C. Solid sodium bromide was removed by suction filtration and one wash of the cake with acetone (50 ml). The solvent was removed using a rotary evaporator to give 187.2 g of a crude viscous yellow oil. Excess 1,4-dibromopentane (34.5 g) was removed by vacuum distillation at 35-40° C./0.3 mm of pressure, leaving 144.6 g (97.7%) of a yellow viscous oil.

Workup

  1. customA one liter, four necked round bottom flask equipped with a mechanical stirrer
  2. customSolid sodium bromide was removed by suction filtration and one
  3. washwash of the cake with acetone (50 ml)
  4. customThe solvent was removed
  5. customa rotary evaporator
  6. customto give 187.2 g of a crude viscous yellow oil
  7. customExcess 1,4-dibromopentane (34.5 g) was removed by vacuum distillation at 35-40° C./0.3 mm of pressure

Sources & evidence

ORD record
ord-a1b99e0247b04454b2e9cf41efcbd917
Source dataset
uspto-grants-2002_11
Patent number
US06479660B1

Reaction notes

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