Hydroquinone → N-[(Morpholin-4-yl)methyl]prop-2-enamide

HRID 1076441Notes

Reaction equation

HRID 1076441 reaction equation
[CH2:1]([NH:3][C:4](=[O:7])[CH:5]=[CH2:6])O.C1(C=CC(O)=CC=1)O.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>O>[N:16]1([CH2:1][NH:3][C:4](=[O:7])[CH:5]=[CH2:6])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 8083MorpholineHCID 13543N-Methylolacrylamide

Product 1

HCID 22725837N-[(Morpholin-4-yl)methyl]prop-2-enamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 300 cc capacity round bottom flask equipped with a stirrer were put 50.5 g (0.5 mole) of N-methylolacrylamide and 50 cc of water and, as a polymerization-inhibitor, 500 mg of hydroquinone. On the other hand, 43 g (0.5 mole) of morpholine were gradually added thereto while stirring. Afterwards, the entire contents were stirred for 1 hour at 50° to 60°C. The reaction product was concentrated and then recrystallized from ethyl acetate. m.p.; 91°-92°C. In addition, the resulting product was further distilled under reduced pressure to obtain 34.5 g of fraction of 140°-160°C/0.01 mmHg (45.7%).

Workup

  1. customIn a 300 cc capacity round bottom flask equipped with a stirrer
  2. stirringAfterwards, the entire contents were stirred for 1 hour at 50° to 60°C
  3. concentrationThe reaction product was concentrated
  4. customrecrystallized from ethyl acetate
  5. distillationIn addition, the resulting product was further distilled under reduced pressure
  6. customto obtain 34.5 g of fraction of 140°-160°C/0.01 mmHg (45.7%)

Sources & evidence

ORD record
ord-50faf706d1b546838207a7334d82a1a2
Source dataset
uspto-grants-1976_05
Patent number
US03957492

Reaction notes

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