Potassium Iodide → N-({4-[(4-Fluorophenyl)methyl]morpholin-2-yl}methyl)acetamide

HRID 1608210Notes

Reaction equation

HRID 1608210 reaction equation
[C:1]([NH:4][CH2:5][CH:6]1[O:11][CH2:10][CH2:9][NH:8][CH2:7]1)(=[O:3])[CH3:2].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)C>[C:1]([NH:4][CH2:5][CH:6]1[O:11][CH2:10][CH2:9][N:8]([CH2:17][C:16]2[CH:19]=[CH:20][C:13]([F:12])=[CH:14][CH:15]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 10241064N-(morpholin-2-ylmethyl)acetamide

Product 1

HCID 10683176N-({4-[(4-Fluorophenyl)methyl]morpholin-2-yl}methyl)acetamideYield 78.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-acetylaminomethylmorpholine (7.0 g), 4-fluorobenzyl chloride (12 g), potassium carbonate (56 g), potassium iodide (1 g), and methyl ethyl ketone (100 ml) is refluxed with stirring for 17 hours. The reaction mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is diluted with water and extracted with chloroform. The organic layer is separated, washed successively with water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure, and the residue is recrystallized from toluene to give the title compound (9.3 g), mp 120°-122° C.

Workup

  1. temperatureis refluxed
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. additionThe residue is diluted with water
  5. extractionextracted with chloroform
  6. customThe organic layer is separated
  7. washwashed successively with water and saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent is distilled off under reduced pressure
  10. customthe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-1e6ab4cb163145839771db2808f111a3
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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