Cesium carbonate → 4-[2-(2-Nitrophenoxy)ethyl]morpholine

HRID 2109960Notes

Reaction equation

HRID 2109960 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[O:11]1[CH2:16][CH2:15][N:14]([CH:17](O)[CH3:18])[CH2:13][CH2:12]1.C(=O)([O-])[O-:21].[Cs+].[Cs+]>CN(C)C=O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:21][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][O:11][CH2:12][CH2:13]1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 30293761-Morpholinoethanol

Product 1

HCID 8673614-[2-(2-Nitrophenoxy)ethyl]morpholine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

As in Example 1 of WO 00/59883, 14.11 g (100 mmol) of 2-fluoronitrobenzene, 14.45 g (100 mmol) of morpholinoethanol, 35.8 g (100 mmol) of cesium carbonate and 100 mL of dimethylformamide were allowed to agitate at room temperature for 7 days. The mixture was then filtered, the dimethylformamide was removed in a rotary evaporator, and the residue was distilled in a bulb tube still at 4 mbar and a furnace temperature of 160 to 170° C.

Workup

  1. filtrationThe mixture was then filtered
  2. customthe dimethylformamide was removed in a rotary evaporator
  3. distillationthe residue was distilled in a bulb tube still at 4 mbar
  4. customa furnace temperature of 160 to 170° C.

Sources & evidence

ORD record
ord-9e10c9e77376474987ad0d0b966fbb38
Source dataset
uspto-grants-2009_04
Patent number
US07517367B2

Reaction notes

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