4-[2-(3-Fluoro-4-nitrophenoxy)ethyl]morpholine → HCID 58307317, compound

HRID 448405Notes

Reaction equation

HRID 448405 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[H][H]>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([O:5][CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:14]=[CH:15][C:16]=1[NH2:17]

Participants

5

Reactant 2

HCID 579358964-[2-(3-Fluoro-4-nitrophenoxy)ethyl]morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 58307317HCID 58307317, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[2-(3-fluoro-4-nitro-phenoxy)-ethyl]-morpholine (2.4 g, 8.9 mmol) and 5% Pd—C (0.3 g) in ethyl acetate (70 mL) was shaken under 50 psi of hydrogen for 20 hours. The mixture was filtered through Celite and evaporated, providing 2.0 g of the product, in 94% yield; 1H NMR (DMSO-d6) δ 2.44 (t, J=4.5, 4H), 2.62 (t, J=5.8 Hz, 2H), 3.57 (t, J=4.5, 4H), 3.95 (t, J=5.8 Hz, 2H), 6.50-6.55 (m, 1H), 6.52-6.72 (m, 2H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-eab6a29d781c48959570080fb298c872
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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