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

HRID 1692462Notes

Reaction equation

HRID 1692462 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-f6b4ad40bd4e4d6db24fd4219b1fc890
Source dataset
uspto-grants-2012_04
Patent number
US08153800B2

Reaction notes

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