4-(3-Nitrophenyl)morpholine → 3-(Morpholin-4-yl)aniline

HRID 31401

Reaction equation

HRID 31401 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>[Pd].C(O)C.CN(C)C=O>[N:10]1([C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=2)[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1

Participants

6

Reactant 2

HCID 12532734-(3-Nitrophenyl)morpholine2×HCID 178418361HCID 178418361, compound

Product 1

HCID 8477683-(Morpholin-4-yl)anilineYield 75.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A flask containing 5% palladium on carbon (1.95 g) was evacuated and refilled with hydrogen. 4-(3-Nitrophenyl)morpholine (intermediate 2) (19.5 g, 93.75 mmol) was introduced into the flask as a solution in ethanol and dimethylformamide (1000 ml, 4:1 v/v). The reaction was stirred at room temperature until further uptake of hydrogen ceased (after approximately 7 L). The reaction was then filtered through celite and solvent removed in vacuo to yield the desired product (12.6 g, 70.6 mmol) as a beige solid.

Workup

  1. customwas evacuated
  2. additionrefilled with hydrogen
  3. filtrationThe reaction was then filtered through celite and solvent
  4. customremoved in vacuo

Sources & evidence

ORD record
ord-a15244507528437e925a9edd6315cfe9
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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