HCID 19828445, compound → 1-[5,5-Bis(4-fluorophenyl)pentyl]-2-piperazinecarboxamide

HRID 1073159Notes

Reaction equation

HRID 1073159 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[CH:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16](CC3C=CC=CC=3)[CH2:15][CH:14]2[C:26]([NH2:28])=[O:27])=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]2[C:26]([NH2:28])=[O:27])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 19828445HCID 19828445, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 150877291-[5,5-Bis(4-fluorophenyl)pentyl]-2-piperazinecarboxamideYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 56.9 parts of 1-[5,5-bis(4-fluorophenyl)-4-pentenyl]-4-(phenylmethyl)-2-piperazinecarboxamide in 400 parts of methanol was hydrogenated in a Parr apparatus and at 50° C. with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was dissolved in 2-propanone and the whole was acidified with a mixture of hydrochloric acid and 2-propanol. After the addition of 2,2'-oxybispropane, the supernatant liquid was decanted and the precipitate was stirred in 2,2'-oxybispropane. The precipitated product was filtered off and dissolved in water. After washing with 2,2'-oxybispropane, the aqueous layer was treated with ammonium hydroxide and the product was extracted with trichloromethane. The extract was washed with a sodium chloride solution, dried, filtered and evaporated (under trichloromethane), yielding 35.2 parts (76.3%) of 1-[5,5-bis(4-fluorophenyl)pentyl]-2-piperazinecarboxamide as a residue (int. 34).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in 2-propanone
  4. additionthe whole was acidified with a mixture of hydrochloric acid and 2-propanol
  5. additionAfter the addition of 2,2'-oxybispropane
  6. customthe supernatant liquid was decanted
  7. filtrationThe precipitated product was filtered off
  8. dissolutiondissolved in water
  9. washAfter washing with 2,2'-oxybispropane
  10. additionthe aqueous layer was treated with ammonium hydroxide
  11. extractionthe product was extracted with trichloromethane
  12. washThe extract was washed with a sodium chloride solution
  13. customdried
  14. filtrationfiltered
  15. customevaporated (under trichloromethane)

Sources & evidence

ORD record
ord-b0f7cec9f0f3432aa090bb85d0c22795
Source dataset
uspto-grants-1990_11
Patent number
US04968684

Reaction notes

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