4-[2-(3-Nitrophenoxy)ethyl]morpholine → 3-(2-Morpholin-4-ylethoxy)aniline

HRID 448396Notes

Reaction equation

HRID 448396 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[O:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[N:10]1([CH2:9][CH2:8][O:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:18]=[CH:17][CH:16]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 29960364-[2-(3-Nitrophenoxy)ethyl]morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 64866163-(2-Morpholin-4-ylethoxy)anilineYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[2-(3-nitro-phenoxy)-ethyl]-morpholine (4.0 g, 13 mmol) and 5% Pd—C (0.3 g) in ethyl acetate (100 mL) was hydrogenated under 50 psi hydrogen for 23 hours. The mixture was filtered through Celite, and the filtrate was evaporated in vacuo, providing 3.0 g, in 86% yield; 1H NMR (CDCl3) δ 2.58 (t, J=4.7 Hz, 4H), 2.78 (t, J=5.8 Hz, 2H), 3.65 (br, 2H), 3.73 (t, J=4.7 Hz, 4H), 4.07 (t, J=5.8 Hz, 2H), 6.24-6.34 (m, 3H), 7.05 (t, J=8.1 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated in vacuo
  3. customproviding 3.0 g

Sources & evidence

ORD record
ord-a4f549bad89d4d25baf31ac812062696
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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