1-Pentene, 5-bromo- → N-Benzylpent-4-en-1-amine

HRID 2240612Notes

Reaction equation

HRID 2240612 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].C(N(C(C)C)CC)(C)C.CO[C:18]1[CH:25]=[C:24](OC)[CH:23]=[CH:22][C:19]=1[CH2:20][NH2:21]>C(#N)C>[CH2:20]([NH:21][CH2:6][CH2:5][CH2:4][CH:3]=[CH2:2])[C:19]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:18]=1

Participants

5

Reactant 3

HCID 707041-Pentene, 5-bromo-HCID 81531DiisopropylethylamineHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 3839348N-Benzylpent-4-en-1-amineYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.397 ml of 5-Bromo-1-pentene (3.35 mmol) and 0.67 ml of diisopropyl ethylamine (3.96 mmol) were added to the reaction solution containing 0.74 ml of benzylamine (a) (4.93 mmol) dissolved in acetonitrile 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 236 mg of the pure title compound (b) (yield: 44%).

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-b46ca452ea5c4dd981c162348aef3d32
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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