Hydroquinone → N-(3-Morpholinopropyl)acrylamide

HRID 1076444Notes

Reaction equation

HRID 1076444 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].C1(C=CC(O)=CC=1)O.[O:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][NH2:23])[CH2:16][CH2:15]1.[OH-].[Na+]>O.C(#N)C>[O:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][NH:23][C:1](=[O:4])[CH:2]=[CH2:3])[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 13140Acryloyl chlorideHCID 14798Sodium HydroxideHCID 61055N-(3-Aminopropyl)morpholine

Product 1

HCID 11735756N-(3-Morpholinopropyl)acrylamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

In a 1 liter capacity round bottom flask equipped with a stirrer were put 90.5 g (1.0 mole) of acrylic acid chloride and 300 cc of acetonitrile and, as a polymerization inhibitor, 0.5 g of hydroquinone, and then, after the contents were cooled to 5°-10°C, 143 g (1.0 mole) of 3-morpholinopropylamine was added dropwise thereto over the course of 3.5 hours while stirring. Afterwards, the reaction mixture was stirred additionally for 2 hours at 40°-50°C. Next, a solution of 40 g of sodium hydroxide in 100 cc of water was added thereto and then the mixture was stirred for 30 minutes. After removal of the sodium chloride which separated, 152 g (77.0%) of a fraction of 144°-146°C/0.1 mmHg were obtained.

Workup

  1. customIn a 1 liter capacity round bottom flask equipped with a stirrer
  2. stirringAfterwards, the reaction mixture was stirred additionally for 2 hours at 40°-50°C
  3. stirringthe mixture was stirred for 30 minutes
  4. customAfter removal of the sodium chloride which
  5. customseparated
  6. custom152 g (77.0%) of a fraction of 144°-146°C/0.1 mmHg were obtained

Sources & evidence

ORD record
ord-7faeb58b06b84401a87e5fa7555f3de7
Source dataset
uspto-grants-1976_05
Patent number
US03957492

Reaction notes

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