7-Bromo-1-heptene → N-(hept-6-enyl)phthalimide

HRID 402160Notes

Reaction equation

HRID 402160 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][CH2:17][CH2:18][CH:19]=[CH2:20]>CN(C=O)C>[CH2:20]([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])[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=[CH2:14]

Participants

4

Reactant 2

HCID 5244507-Bromo-1-hepteneHCID 24194345Phthalimide potassium salt

Product 1

HCID 53236045N-(hept-6-enyl)phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of potassium phthalimide (627 mg, 3.38 mmol) and 7-bromohept-1-ene in dry DMF (10 mL) was stirred at 100° C. under nitrogen for 1 h. Then, the reaction mixture was successively cooled to room temperature, filtered, diluted with ether, and filtered again. The filtrate was concentrated under reduced pressure to give the target product 75 as an oil, which was used without further purifications in the next step: m/z=244 (M+H)+.

Workup

  1. filtrationfiltered
  2. additiondiluted with ether
  3. filtrationfiltered again
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-523896de0abd4407a2547d80ef65f7c7
Source dataset
uspto-grants-2014_06
Patent number
US08741926B2

Reaction notes

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