Lead dioxide → 1,1-Bis(4-morpholinophenyl)ethylene

HRID 1199113Notes

Reaction equation

HRID 1199113 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:20][CH:19]=3)(C)[C:14](O)=O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[Pb](=O)=O>C1(C)C=CC=CC=1>[O:27]1[CH2:28][CH2:29][N:24]([C:21]2[CH:20]=[CH:19][C:18]([C:13]([C:10]3[CH:11]=[CH:12][C:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)=[CH:8][CH:9]=3)=[CH2:14])=[CH:23][CH:22]=2)[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 14793Lead dioxideHCID 142278772,2-Bis(4-morpholinophenyl)propionic acid

Product 1

HCID 143237971,1-Bis(4-morpholinophenyl)ethyleneYield 46.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into 200 ml of toluene was dissolved 10 g of 2,2-bis(4-morpholinophenyl)propionic acid. Thereto was added 7.2 g of lead dioxide and the mixture was reacted at reflux temperature with stirring for one hour. The lead compound was removed by filtration and the toluene layer was extracted with 200 ml of 3% aqueous solution of sodium hydroxide to recover the unreacted starting material. The remained toluene solution was concentrated at a reduced pressure to obtain crystals. The crystal was recrystallized from n-propanol to obtain 4.1 g (yield 46.3%) of 1,1-bis(4-morpholinophenyl)ethylene, having a melting point of 203°~205° C. The starting 2,2-bis(4-morpholinophenyl)propionic acid was recovered in an amount of 3.8 g.

Workup

  1. customthe mixture was reacted
  2. temperatureat reflux temperature
  3. customThe lead compound was removed by filtration
  4. extractionthe toluene layer was extracted with 200 ml of 3% aqueous solution of sodium hydroxide
  5. customto recover the
  6. concentrationThe remained toluene solution was concentrated at a reduced pressure
  7. customto obtain crystals
  8. customThe crystal was recrystallized from n-propanol

Sources & evidence

ORD record
ord-b83d69f3378c4e43b470d60f0c792f31
Source dataset
uspto-grants-1990_02
Patent number
US04898941

Reaction notes

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