Potassium Iodide → 1-[4,4-Bis(4-fluorophenyl)butyl]-4-(phenylmethyl)-2-piperazinecarboxamide

HRID 35318Notes

Reaction equation

HRID 35318 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH:10]([C:14]([NH2:16])=[O:15])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:18][CH2:19][CH2:20][CH:21]([C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[F:28][C:25]1[CH:24]=[CH:23][C:22]([CH:21]([C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[CH2:20][CH2:19][CH2:18][N:11]2[CH2:12][CH2:13][N:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:9][CH:10]2[C:14]([NH2:16])=[O:15])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 142302664-Benzylpiperazine-2-carboxamide

Product 1

HCID 212956801-[4,4-Bis(4-fluorophenyl)butyl]-4-(phenylmethyl)-2-piperazinecarboxamideYield 63.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 13.2 parts of 4-(phenylmethyl)-2-piperazinecarboxamide, 18.5 parts of 1,1'-(4-chlorobutylidene)bis[4-fluorobenzene], 14.8 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone was stirred and refluxed for 72 hours using a water-separator. The reaction mixture was cooled to room temperature, filtered and the filtrate was evaporated. The oily residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 17.7 parts (63.6%) of 1-[4,4-bis(4-fluorophenyl)butyl]-4-(phenylmethyl)-2-piperazinecarboxamide; mp. 79.2° C. (intermediate 46).

Workup

  1. temperaturerefluxed for 72 hours
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. customThe oily residue was purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from 2,2'-oxybispropane
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-3d67199ab52d4a9abc533d0974e52a7b
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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