Homoallyl bromide → HCID 57443426, compound

HRID 2240593Notes

Reaction equation

HRID 2240593 reaction equation
Br[CH2:2][CH2:3][CH:4]=[CH2:5].C(N(C(C)C)CC)(C)C.[CH3:15][O:16][C:17]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20]>C(Cl)Cl>[CH2:2]([NH:20][CH2:19][C:18]1[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:17]=1[O:16][CH3:15])[CH2:3][CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 21241Homoallyl bromideHCID 81531DiisopropylethylamineHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 57443426HCID 57443426, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.5 ml of 1-Bromo-3-butene (4.926 mM) and 0.94 ml of diisopropyl ethylamine (5.396 mM) were added to the reaction solution containing 0.74 ml of 2,4-dimethoxybenzylamine (a) (4.926 mM) dissolved in methylene chloride with stirring and the solution was left alone at room temperature for overnight. The reaction mixture was washed with saturated NaCl solution, dried over MgSO4, filtered and concentrated in vacuo. The resulting compound was purified with Silica gel column chromatography with EtOAc solvent as an eluant to give 436 mg of the pure title compound (b) (yield: 40%).

Workup

  1. washThe reaction mixture was washed with saturated NaCl solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting compound was purified with Silica gel column chromatography with EtOAc solvent as an eluant

Sources & evidence

ORD record
ord-7182579dc9fc45ec8dd391fcf533aeb9
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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