4-[2-(4-Nitrophenoxy)ethyl]morpholine → 4-(2-Morpholinoethoxy)aniline

HRID 1366146Notes

Reaction equation

HRID 1366146 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[OH-].[Pd+2].[OH-]>[N:11]1([CH2:10][CH2:9][O:8][C:7]2[CH:17]=[CH:18][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 8008814-[2-(4-Nitrophenoxy)ethyl]morpholine

Product 1

HCID 64847114-(2-Morpholinoethoxy)anilineYield 63.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-[2-(4-nitro-phenoxy)-ethyl]-morpholine (2.25 g, 8.93 mmol) in ethanol (40 mL) is added palladium hydroxide (0.313 g, 0.45 mmol) and the mixture is stirred in a Parr-apparatus under hydrogen pressure (5 bars) for 2 hours. Filtration over Celite 521 and evaporation gave a red oil purified by silica gel column chromatography. Elution with DCM and a mixture 90:10 DCM:MeOH affords the title compound as a white solid (1.256 g, 63%). 1H-NMR (400 MHz, CDCl3) δ (ppm).2.52-2.63 (4H, m), 2.71-2.80 (2H, t), 3.46 (2H, br s), 3.70-3.78 (4H, m), 4.00-4.10 (2H, m), 6.65 (2H, d), 6.77 (2H, d).

Workup

  1. filtrationFiltration
  2. customover Celite 521 and evaporation
  3. customgave a red oil
  4. custompurified by silica gel column chromatography
  5. washElution with DCM

Sources & evidence

ORD record
ord-665a297e92e34c8c8cc98fcb381fedc3
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

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