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

HRID 639377Notes

Reaction equation

HRID 639377 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.[Pd]>[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)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8.1 g (32 mMol) of 4-[2-(4-Nitro-phenoxy)-ethyl]-morpholine is dissolved in 100 mL of ethanol and subjected to catalytic hydration at rt using 681 mg of Pd/C. After filtration trough HYFLO and removal of the solvent under reduced pressure, the crude product is purified by bulb-to-bulb distillation (0.13 mbar: 200° C.) to obtain 4-(2-morpholin-4-yl-ethoxy)-phenylamine. Title compound: ES-MS: 223 [M+H]+; single peak at tR=3 min (System 2).

Workup

  1. customsubjected to catalytic hydration at rt
  2. filtrationAfter filtration trough HYFLO and removal of the solvent under reduced pressure
  3. distillationthe crude product is purified by bulb-to-bulb distillation (0.13 mbar: 200° C.)

Sources & evidence

ORD record
ord-221a1057335040f79458062619b8e526
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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