Water → HCID 9883176, compound

HRID 654837Notes

Reaction equation

HRID 654837 reaction equation
[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[O:6][CH:7]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8](OCC)=O)[CH3:2].[CH2:24]([NH2:27])[CH2:25][NH2:26].C[Al](C)C.O>C1(C)C=CC=CC=1.CO>[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[O:6][CH:7]([C:8]1[NH:26][CH2:25][CH2:24][N:27]=1)[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 16682925TrimethylaluminumHCID 19886523HCID 19886523, compound

Product 1

HCID 9883176HCID 9883176, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

A mixture of 6.28 g (0.02 m) of ethyl 2-(2-ethoxy-phenoxy)-3-phenylpropionate, 1.93 g (0.033 m) ethylenediamine and 150 ml of dry toluene was stirred at room temperature and 17 ml of a 2 m solution of trimethylaluminum in toluene was added dropwise. After stirring 10 minutes, the mixture was heated at reflux for 3 hours, then cooled in an ice bath. Water (10 ml) was added followed by 20 ml methanol and the mixture heated on a steam bath for 0.5 hours. Solids were filtered and the solvent evaporated. The solid residue was recrystallized from cyclohexane to give 3.53 g, melting point 95-97° C. Anal., Calcd. for C19H22N2O2 : C=73.52; H=7.14; N=9.0,

Workup

  1. stirringAfter stirring 10 minutes
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 3 hours
  4. temperaturecooled in an ice bath
  5. temperaturethe mixture heated on a steam bath for 0.5 hours
  6. filtrationSolids were filtered
  7. customthe solvent evaporated
  8. customThe solid residue was recrystallized from cyclohexane
  9. customto give 3.53 g, melting point 95-97° C

Sources & evidence

ORD record
ord-fa2b5128926e4f0bbc2c3b9dcfb81c97
Source dataset
uspto-grants-1992_07
Patent number
US05134154

Reaction notes

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