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

HRID 448393

Reaction equation

HRID 448393 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.[H][H]>C(OCC)(=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

5

Reactant 2

HCID 8008814-[2-(4-Nitrophenoxy)ethyl]morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 64847114-(2-Morpholinoethoxy)anilineYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[2-(4-nitro-phenoxy)-ethyl]-morpholine (3.2 g, 13 mmol) and 5% Pd—C (0.3 g) in ethyl acetate (70 mL) was hydrogenated under 50 psi hydrogen for 20 hours. The mixture was filtered through Celite, and the filtrate was evaporated in vacuo, providing 2.0 g, in 72% yield; 1H NMR (CDCl3) δ 2.57 (t, J=4.6 Hz, 4H), 2.77 (t, J=5.8 Hz, 2H), 3.74 (t, J=4.6 Hz, 4H), 4.04 (t, J=5.8 Hz, 2H), 6.63 (d, J=8.8 Hz, 2H), 6.75 (d, J=8.8 Hz, 2H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated in vacuo
  3. customproviding 2.0 g

Sources & evidence

ORD record
ord-2fca45d249b74f8dbbc330c160847dcc
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Linked notes

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