Sodium Iodide → HCID 22185398, compound

HRID 601033Notes

Reaction equation

HRID 601033 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[O:14][CH3:15].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)C.ClCCl>[CH3:15][O:14][C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 22326897HCID 22326897, compound

Product 1

HCID 22185398HCID 22185398, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2-chloro-ethoxy)-2-methoxy-4-nitro-benzene (0.60 g, 2.59 mmol), morpholine (0.28 mL, 3.11 mmol), sodium iodide (0.39 g, 2.59 mmol) and potassium carbonate (0.71 g, 5.18 mmol), in ethanol (5 mL) was heated in a sealed tube at 90° C. for 18 h, was cooled, filtered and evaporated. Purification by flash chromatography (SiO2) eluted with 2:98 methanol:dichloromethane provided 4-[2-(2-methoxy-4-nitro-phenoxy)-ethyl]-morpholine (0.37 g, 51% yield) as a pale yellow solid. 1H-NMR (DMSO-d6, 500 MHz) 7.89 (dd, 1H), 7.74 (d, 1H), 7.21 (d, 1H), 4.23 (t, 2H), 3.88 (s, 3H), 3.88 (m, 4H), 2.73 (t, 2H), 2.50 (m, 4H) ppm; MS (FIA) 283.2 (M+H); HPLC (Method A) 2.652 min.

Workup

  1. temperaturewas cooled
  2. filtrationfiltered
  3. customevaporated
  4. customPurification by flash chromatography (SiO2)
  5. washeluted with 2:98 methanol

Sources & evidence

ORD record
ord-a863a460f7d94179905015900a63d714
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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