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

HRID 35319Notes

Reaction equation

HRID 35319 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15](CC3C=CC=CC=3)[CH2:14][CH:13]2[C:25]([NH2:27])=[O:26])=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH:13]2[C:25]([NH2:27])=[O:26])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 212956801-[4,4-Bis(4-fluorophenyl)butyl]-4-(phenylmethyl)-2-piperazinecarboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 138832881-[4,4-Bis(4-fluorophenyl)butyl]-2-piperazinecarboxamideYield 66.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 14.8 parts of 1-[4,4-bis(4-fluorophenyl)butyl]-4-(phenylmethyl)-2-piperazinecarboxamide and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 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. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (85:15 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane, yielding 7.9 parts (66.4%) of 1-[4,4-bis(4-fluorophenyl)butyl]-2-piperazinecarboxamide; m.p. 113.6° C. (intermediate 53).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (85:15 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-87164c71da6b490c94839b1f49e4f1fe
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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