N-Ethylaniline → HCID 13264654, compound

HRID 252021Notes

Reaction equation

HRID 252021 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[CH2:10](Br)[CH:11]=[CH2:12].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O.CCOC(C)=O>[CH2:10]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:11]=[CH2:12]

Participants

7

Reactant 3

HCID 7670N-EthylanilineHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 13264654HCID 13264654, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl-phenyl-amine (4.15 mL, 33 mmol), allyl bromide (4.3 mL, 1.5 eq.) and K2CO3 (9.1 g, 2.0 eq.) in acetone (50 mL) was heated at reflux for overnight. After cooling to room temperature, the reaction mixture was diluted with water (50 mL) and EtOAc (100 m). The separated organic phase was dried over Na2SO4, filtered and concentrated and the product was purified by chromatography (10% EtOAc/hexanes) to give allyl-ethyl-phenyl-amine (5.32 g, 100%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for overnight
  3. dry with materialThe separated organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe product was purified by chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e025c43081d34608a00b9d36ca77e0d8
Source dataset
uspto-grants-2011_01
Patent number
US07868002B2

Reaction notes

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