Potassium Carbonate → 4-[2-(3-Fluoro-4-nitrophenoxy)ethyl]morpholine

HRID 448404Notes

Reaction equation

HRID 448404 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Cl.Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[O:11][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 579358964-[2-(3-Fluoro-4-nitrophenoxy)ethyl]morpholineYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-fluoro-4-nitrophenol (1.6 g, 10 mmol), 4-(2-chloroethyl)morpholine hydrochloride (1.9 g, 10 mmol), and potassium carbonate (5.5 g, 52 mmol) in acetone (50 mL) was heated to reflux with stirring for 16 hours. The mixture was cooled and evaporated under vacuum. The residue was partitioned between water (100 mL) and ethyl acetate (100 mL), and the organic phase was washed with water (100 mL) and brine (100 mL), was dried (MgSO4), and evaporated, providing 2.6 g, in 93% yield; 1H NMR (DMSO-d6) δ 2.47 (t, 4H, J=4.6), 2.71 (t, J=5.6 Hz, 2H), 3.57 (t, J=4.6, 4H), 4.25 (t, J=5.6 Hz, 2H), 6.99 (dd, J=9.3 Hz, J=2.7 Hz, 1H), 7.19-7.24 (m, 1H), 8.14 (t, J=9.3 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe mixture was cooled
  4. customevaporated under vacuum
  5. customThe residue was partitioned between water (100 mL) and ethyl acetate (100 mL)
  6. washthe organic phase was washed with water (100 mL) and brine (100 mL)
  7. dry with materialwas dried (MgSO4)
  8. customevaporated
  9. customproviding 2.6 g

Sources & evidence

ORD record
ord-c2a8e76c0c6c4250b45dfe32e97a71ea
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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