Allyl bromide → HCID 21330400, compound

HRID 616547Notes

Reaction equation

HRID 616547 reaction equation
[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH2:17][CH3:18])([CH3:16])[NH:13][C:12]([CH2:20][CH3:21])([CH3:19])[CH:11]1[CH3:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23](Br)[CH:24]=[CH2:25]>CN(C)C=O>[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH2:17][CH3:18])([CH3:16])[N:13]([CH2:25][CH:24]=[CH2:23])[C:12]([CH2:20][CH3:21])([CH3:19])[CH:11]1[CH3:22])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 20340209HCID 20340209, compound

Product 1

HCID 21330400HCID 21330400, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6.0 g of 2,6-diethyl-2,3,6-trimethyl-4-piperidyl benzoate (Compound 10 - prepared using the same procedure as is described in Preparation 2) in 20 ml of dimethylformamide were added 6.0 g of allyl bromide, and the mixture was heated at 110° - 115° C for 9 hours. The mixture was then concentrated by evaporation under reduced pressure and 50 ml of benzene were added. The resulting mixture was then washed, in turn, with an aqueous solution of sodium carbonate and with water and was then dried over anhydrous sodium sulphate. After removing the solvent, the residue was distilled under reduced pressure, giving 1.6 g of Compound 36 as a colourless, viscous liquid (bp 163° C/0.004 mmHg).

Workup

  1. temperaturethe mixture was heated at 110° - 115° C for 9 hours
  2. concentrationThe mixture was then concentrated by evaporation under reduced pressure and 50 ml of benzene
  3. additionwere added
  4. washThe resulting mixture was then washed, in turn, with an aqueous solution of sodium carbonate and with water
  5. dry with materialwas then dried over anhydrous sodium sulphate
  6. customAfter removing the solvent
  7. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-267030da8da04028bc9669f8f921456c
Source dataset
uspto-grants-1978_02
Patent number
US04075165

Reaction notes

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