Potassium Iodide → 3-(aminocarbonyl)-4-[4,4-bis(4-fluorophenyl)pentyl]-N-(2,6-dichlorophenyl)-1-piperazineacetamide dihydrochloride monohydrate

HRID 35336Notes

Reaction equation

HRID 35336 reaction equation
[Cl:1]C[CH2:3][CH2:4][CH2:5][CH:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[NH2:21][C:22]([CH:24]1[NH:29][CH2:28][CH2:27][N:26]([CH2:30][C:31]([NH:33][C:34]2[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:41])=[O:32])[CH2:25]1)=[O:23].[C:42](=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(C)CC(=O)C>[OH2:23].[ClH:1].[ClH:40].[NH2:21][C:22]([CH:24]1[N:29]([CH2:3][CH2:4][CH2:5][C:6]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH3:42])[CH2:28][CH2:27][N:26]([CH2:30][C:31]([NH:33][C:34]2[C:35]([Cl:41])=[CH:36][CH:37]=[CH:38][C:39]=2[Cl:40])=[O:32])[CH2:25]1)=[O:23]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 142302313-Carbamoyl-N-(2,6-dichlorophenyl)piperazine-1-acetamideHCID 150877141,1'-(5-Chloropentylidene)bis(4-fluorobenzene)

Product 1

HCID 867423893-(aminocarbonyl)-4-[4,4-bis(4-fluorophenyl)pentyl]-N-(2,6-dichlorophenyl)-1-piperazineacetamide dihydrochloride monohydrate

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5 parts of 1,1'-(5-chloropentylidene)bis(4-fluorobenzene), 5 parts of 3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-1-piperazineacetamide, 2.2 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone was stirred and refluxed for 24 hours. The reaction mixture was cooled and purified by column-chromatography (2x) over silica gel using first a mixture of trichloromethane and methanol (95:5 by volume) and then a mixture of trichloromethane and methanol (97:3 by volume) as eluents. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in acetonitrile and 2-propanol. After stirring for one hour at room temperature, the salt was filtered off and dried, yielding 1.53 parts of 3-(aminocarbonyl)-4-[4,4-bis(4-fluorophenyl)pentyl]-N-(2,6-dichlorophenyl)-1-piperazineacetamide dihydrochloride monohydrate; mp. 206.2° C. (compound 49).

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureThe reaction mixture was cooled
  3. custompurified by column-chromatography (2x) over silica gel using first
  4. additiona mixture of trichloromethane and methanol (95:5 by volume)
  5. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluents
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. stirringAfter stirring for one hour at room temperature
  9. filtrationthe salt was filtered off
  10. customdried

Sources & evidence

ORD record
ord-88d463e497774174bbe53dcf131560d6
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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