4-[2-(3-Methoxy-4-nitrophenoxy)ethyl]morpholine → HCID 58748494, compound

HRID 448367Notes

Reaction equation

HRID 448367 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[N+:18]([O-])=O)[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:15]=[CH:16][C:17]=1[NH2:18]

Participants

5

Reactant 2

HCID 587483904-[2-(3-Methoxy-4-nitrophenoxy)ethyl]morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 58748494HCID 58748494, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[2-(3-methoxy-4-nitrophenoxy)ethyl]morpholine (1.2 g, 4.3 mmol) and 5% Pd—C (0.2 g) in ethyl acetate (75 mL) was shaken under 50 psi of hydrogen for 24 hours. The mixture was filtered through Celite and evaporated, providing 0.95 g of the product as a light grey oil, in 87% yield: 1H NMR (CDCl3) δ 2.57 (t, J=4.6 Hz, 4H), 2.77 (t, J=5.7 Hz, 2H), 3.74 (t, J=4.6 Hz, 4H), 3.82 (s, 3H), 4.05 (t, J=5.7 Hz, 2H), 6.34 (dd, J=8.4 Hz, J=2.5 Hz, 1H), 6.47 (d, J=2.5 Hz, 1H), 6.63 (d, J=8.4 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-e7459112349e40c8bf57dba04d9e5ba5
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

Loading…