Potassium Iodide → HCID 21545454, compound

HRID 1605860Notes

Reaction equation

HRID 1605860 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH:8](Br)[CH2:9][CH2:10]Cl)=[O:7])=[CH:4][CH:3]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.[I-].[K+]>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH:8]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH2:9][CH2:10][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8083MorpholineHCID 30165872-Bromo-4-chloro-1-(4-fluorophenyl)butan-1-one

Product 1

HCID 21545454HCID 21545454, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 10 g. of 1-p-fluorobenzoyl-1-bromo-3-chloro-propane, 12.5 g. of morpholine and a catalytic quantity of potassium iodide in 100 cc. xylene is made to reflux for 12 hours and then cooled. The resulting solid is filtered and the filtrate extracted with dilute HCl. The separated aqueous phase is filtered hot using animal charcoal, cooled, made alkaline with dilute soda solution, and extracted with diethyl ether. The organic phases are combined, washed with water, dried and evaporated, m.p. : 82°C (from hexane).

Workup

  1. temperatureto reflux for 12 hours
  2. temperaturecooled
  3. filtrationThe resulting solid is filtered
  4. extractionthe filtrate extracted with dilute HCl
  5. filtrationThe separated aqueous phase is filtered hot using animal charcoal
  6. temperaturecooled
  7. additionwith dilute soda solution
  8. extractionextracted with diethyl ether
  9. washwashed with water
  10. customdried
  11. customevaporated
  12. custom82°C (from hexane)

Sources & evidence

ORD record
ord-06d7bc3e1698455089128f9550a7c048
Source dataset
uspto-grants-1976_04
Patent number
US03951978

Reaction notes

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