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

HRID 1784382Notes

Reaction equation

HRID 1784382 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>CO.[Pd]>[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

4

Reactant 1

HCID 12532734-(3-Nitrophenyl)morpholine

Product 1

HCID 8477683-(Morpholin-4-yl)anilineYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a cooled (0° C.) solution of 4-(3-nitro-phenyl)-morpholine (43)(4.16 g, 20 mmol) in methanol (50 ml) was added Pd/C (10% loading, 460 mg). The mixture was stirred at room temperature under an H2 (1 atm) for 16 hrs. The mixture was then filtered through a Celite™ pad, the filtrate dried using MgSO4, filtered and concentrated in vacuo to give the title compound (3.39 g, 95.2%) as an orange solid that was suitably clean to be used without any further purification. m/z (LC-MS, ESP): 179 [M+H]+, R/T=1.69 mins.

Workup

  1. filtrationThe mixture was then filtered through a Celite™ pad
  2. customthe filtrate dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8513643c609c4e298d82a8cb8e6aed0e
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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