Potassium Iodide → HCID 22368226, compound

HRID 1494652Notes

Reaction equation

HRID 1494652 reaction equation
[Cl:1]CCCCC(C1C=CC(F)=CC=1)C1C=CC(F)=CC=1.NC([CH:24]1[NH:29][CH2:28][CH2:27][N:26]([CH2:30][C:31]([NH:33][C:34]2[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=2[CH3:41])=[O:32])[CH2:25]1)=O.[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C(N(CC)CC)C>[ClH:1].[F:40][C:38]1[CH:37]=[CH:36][C:35]([CH3:41])=[C:34]([NH:33][C:31](=[O:32])[CH2:30][N:26]2[CH2:25][CH2:24][NH:29][CH2:28][CH2:27]2)[CH:39]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 14722540HCID 14722540, compoundHCID 150877141,1'-(5-Chloropentylidene)bis(4-fluorobenzene)

Product 1

HCID 22368226HCID 22368226, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.5 parts of 1,1'-(5-chloro-1-pentylidene)bis[4-fluorobenzene], 2.94 parts of 3-(aminocarbonyl)-N-(5-fluoro-2-methylphenyl)-1-piperazineacetamide, 2.1 parts of N,N-diethylethanamine, 0.1 parts of potassium iodide and 45 parts of N,N-dimethylformamide was stirred and heated for 48 hours at about 70° C. After 24 hours of stirring 2.12 parts of sodium carbonate were added. The reaction mixture was evaporated. The residue was taken up in water and the product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in acetonitrile, 2-propanol and a few drops of water. The salt was filtered off and dried over weekend at 100° C., yielding 1.70 parts of 3-(aminocarbonyl)-4-5,5-bis(4-fluorophenyl)pentyl]-N-(5-fluoro-2-methylphenyl)-1-piperazineacetamide monohydrochloride; mp. 217.8° C. (compound 3).

Workup

  1. additionwere added
  2. customThe reaction mixture was evaporated
  3. extractionthe product was extracted with dichloromethane
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. filtrationThe salt was filtered off
  13. customdried over weekend at 100° C.

Sources & evidence

ORD record
ord-6939fc868ff34556b0d7562c5f8959db
Source dataset
uspto-grants-1991_06
Patent number
US05026853

Reaction notes

Loading…