Sodium Iodide → 4-[2-(4-Methyl-3-nitrophenoxy)ethyl]morpholine

HRID 1158081Notes

Reaction equation

HRID 1158081 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C([O-])([O-])=O.[Cs+].[Cs+].[Na+].[I-]>CN(C=O)C.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 162713-Nitro-p-cresolHCID 767274-(2-Chloroethyl)morpholine

Product 1

HCID 589298674-[2-(4-Methyl-3-nitrophenoxy)ethyl]morpholine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-methyl-3-nitrophenol (1.53 g, 10 mmol.), 4-(2-chloroethyl)morpholine (2.79 g, 15 mmol), Cs2CO3 (9.78 g, 30 mmol) and NaI (145 mg, 1 mmol) in DMF (15 mL) was stirred for 3 h at 80° C. The reaction mixture was then cooled to room temperature, diluted with water, and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (4:1:0.05 CH2Cl2/EtOAc/MeOH) to give the title compound as an oil.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash chromatography (4:1:0.05 CH2Cl2/EtOAc/MeOH)

Sources & evidence

ORD record
ord-d491bc4f96984006a7c7b5923dc63afb
Source dataset
uspto-grants-2010_10
Patent number
US07807700B2

Reaction notes

Loading…