Sodium Iodide → HCID 63068513, compound

HRID 447927Notes

Reaction equation

HRID 447927 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[OH:11])=[O:3].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+].[Na+].[I-]>CC(C)=O>[F:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[C:5]([O:11][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:6]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 27373264'-Fluoro-2'-hydroxyacetophenone

Product 1

HCID 63068513HCID 63068513, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.5 g (3.24 mmol) 4-fluoro-2-hydroxyacetophenone, 720 mg (3.87 mmol) N-(2-chloroethyl)morpholine hydrochloride, 900 mg K2CO3 and a catalytic amount of NaI in 20 ml acetone were heated for 20 hours at reflux. The mixture was concentrated, was dissolved in dichloromethane, was washed with water and saturated NaCl solution, was dried and was concentrated once again. Chromatography of the crude product on silica gel (dichloromethane/methanol 0-4%) yielded 730 mg of a clear, colorless oil; ESI-MS [M+H+]=268.15.

Workup

  1. temperatureat reflux
  2. concentrationThe mixture was concentrated
  3. dissolutionwas dissolved in dichloromethane
  4. washwas washed with water and saturated NaCl solution
  5. customwas dried
  6. concentrationwas concentrated once again

Sources & evidence

ORD record
ord-a887a5a4c4ec41c4ab95bbff0aa0fe3d
Source dataset
uspto-grants-2013_07
Patent number
US08481576B2

Reaction notes

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