Homoallyl bromide → HCID 57443426, compound

HRID 2261391Notes

Reaction equation

HRID 2261391 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 (4.93 mmol) and 0.94 ml of diisopropyl ethylamine (5.40 mmol) were added to the reaction solution containing 0.74 ml of 2,4-dimethoxybenzylamine (a) (4.93 mmol) dissolved in methylene chloride with stirring and the mixture was stirred 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. stirringthe mixture was stirred at room temperature for overnight
  2. washThe reaction mixture was washed with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting compound was purified with Silica gel column chromatography with EtOAc solvent as an eluant

Sources & evidence

ORD record
ord-8d65a25d1b574332a06796ec87c3d77c
Source dataset
uspto-grants-2010_12
Patent number
US07846963B2

Reaction notes

Loading…