Allyl bromide → HCID 54396564, compound

HRID 2259435Notes

Reaction equation

HRID 2259435 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[CH2:5]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(O)C>[CH2:5]([N:14]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][CH:2]=[CH2:1])[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 3937474HCID 3937474, compound

Product 1

HCID 54396564HCID 54396564, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.0 g (90 mmol) of allyl bromide were added to 10.0 g (44.8 mmol) of N-cinnamylbenzylamine in 60 ml of ethanol, and then 5.0 g (50.0 mmol) of triethylamine were added while stirring. The mixture was refluxed for 4 h. Concentration under water pump vacuum was followed by partition of the contents of the flask between methylene chloride and water, rendition alkaline with dilute sodium hydroxide solution and extraction twice more with methylene chloride. The combined organic phases were washed with dilute sodium hydroxide solution, dried and concentrated. The crude product (12.5 g) was purified by column chromatography (silica gel, mobile phase methylene chloride/methanol 98/2). 9.2 g (80%) of product (oil) were obtained.

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. concentrationConcentration under water pump vacuum
  3. customby partition of the contents of the flask between methylene chloride and water, rendition alkaline with dilute sodium hydroxide solution and extraction twice more with methylene chloride
  4. washThe combined organic phases were washed with dilute sodium hydroxide solution
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product (12.5 g) was purified by column chromatography (silica gel, mobile phase methylene chloride/methanol 98/2)

Sources & evidence

ORD record
ord-01fd0d74c336487db5ec272954bc21ce
Source dataset
uspto-grants-1995_12
Patent number
US05473080

Reaction notes

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