Morpholine → 4-(2-Methoxy-4-nitrophenyl)morpholine

HRID 601501Notes

Reaction equation

HRID 601501 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[O:17][CH3:18]>>[CH3:18][O:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 705192-Chloro-5-nitroanisole

Product 1

HCID 219364654-(2-Methoxy-4-nitrophenyl)morpholineYield 18.6%

Conditions

Temperature
100 °C

Procedure

Mix morpholine (1.50 mL, 17.20 mmol) and 1-chloro-2-methoxy-4-nitro-benzene (1.06 g, 5.65 mmol) and heat to 100° C. for 4 h while stirring. Cool the solution to room temperature, then partition between EtOAc (40 mL) and 1N HCl (20 mL). Wash the organic solution with water (20 mL) and brine (20 mL), dry, filter, and concentrate. Purify the crude material by flash chromatography, using a linear gradient of 100% hexanes to 50% EtOAc/hexanes, to give the title compound as a yellow solid (250 mg, 18%). MS (ES+) 239.0 (M+1)+. 1H NMR (400 MHz, CDCl3) δ: 7.86 (dd, 1H, J=8.8, 2.6 Hz), 7.71 (d, 1H, J=2.2 Hz), 6.87 (d, 1H, J=9.2 Hz), 3.94 (s, 31), 3.87 (m, 4H), 3.21 (m, 4H).

Workup

  1. temperatureCool the solution to room temperature
  2. custompartition between EtOAc (40 mL) and 1N HCl (20 mL)
  3. washWash the organic solution with water (20 mL) and brine (20 mL)
  4. customdry
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude material by flash chromatography

Sources & evidence

ORD record
ord-89af306f98ce42e4bf4afca8ac0b3a49
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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