Allyl bromide → HCID 4722371, compound

HRID 2261368Notes

Reaction equation

HRID 2261368 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].C(N(C(C)C)CC)(C)C.[CH3:14][O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].[OH-].[Na+]>C(Cl)Cl>[CH2:1]([NH:19][CH2:18][C:17]1[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:16]=1[O:15][CH3:14])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 4722371HCID 4722371, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.32 ml of allylbromide (3.66 mmol) and 0.7 ml of diisopropyl ethylamine (3.99 mmol) were added to the reaction solution containing 500 mg of 2,4-dimethoxybenzylamine (3.33 mmol) dissolved in methylene chloride with stirring and the solution was left alone at room temperature. After the reaction mixture was neutralized with 10% NaOH solution, the mixture was extracted with chloroform, washed with saturated NaCl solution, dried over MgSO4, filtered, and concentrated in vacuo. The resulting compound was purified with Silica gel column chromatography with a solvent mixture mixed with methanol and chloroform (1:9) as an eluant to give 276 mg of allyl-(2,4-dimethoxybenzyl)amine (1b) (yield: 40%).

Workup

  1. waitthe solution was left alone at room temperature
  2. extractionthe mixture was extracted with chloroform
  3. washwashed with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting compound was purified with Silica gel column chromatography with a solvent mixture
  8. additionmixed with methanol and chloroform (1:9) as an eluant

Sources & evidence

ORD record
ord-18a2ab6d49604b5a8b554753bf5f40e5
Source dataset
uspto-grants-2010_12
Patent number
US07846963B2

Reaction notes

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