Acrylonitrile → N-(3-Aminopropyl)morpholine

HRID 375009Notes

Reaction equation

HRID 375009 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7](#[N:10])[CH:8]=[CH2:9]>C(N(CC)CC)C>[NH2:10][CH2:7][CH2:8][CH2:9][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 8083Morpholine

Product 1

HCID 61055N-(3-Aminopropyl)morpholine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

One mole of morpholine is reacted with 1.1 moles of acrylonitrile, added at about 28° C. with about 0.05 moles of a basic triamine, such as triethylamine, as a catalyst. The reaction is exothermic. After stirring for about 5 hours, the reaction mixture is distilled free of unreacted acrylonitrile. The resulting acrylonitrile adduct is reduced to the amine at 100° C. -150° C. under 1000 psig hydrogen using a copper catalyst. The resulting product is distilled to purity.

Workup

  1. distillationthe reaction mixture is distilled free of unreacted acrylonitrile
  2. customis reduced to the amine at 100° C. -150° C. under 1000 psig hydrogen using
  3. distillationThe resulting product is distilled to purity

Sources & evidence

ORD record
ord-b0d38cb3fee94aa2b2e90e643f6d6cb2
Source dataset
uspto-grants-1996_01
Patent number
US05484462

Reaction notes

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