Methane → 1-[3,3-Bis(4-fluorophenyl)propyl]piperazine

HRID 2255140Notes

Reaction equation

HRID 2255140 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16](CC3C=CC=CC=3)[CH2:15][CH2:14]2)=[CH:6][CH:5]=1.C>CO.O.[Pd]>[F:32][C:29]1[CH:28]=[CH:27][C:26]([CH:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)[CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 297MethaneHCID 200879611-[3,3-Bis(4-fluorophenyl)-2-propenyl]-4-(phenylmethyl)piperazine dihydrochloride

Product 1

HCID 138832821-[3,3-Bis(4-fluorophenyl)propyl]piperazineYield 99.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 32,5 g of 1-[3,3-bis(4-fluorophenyl)-2-propenyl]-4-(phenylmethyl)piperazine dihydrochloride and 3,3 g of 5% Pd at activated charcoal in 150 ml of methanol and 100 ml of water was hydrogenated under 60 psi. The catalyst was filtered off and after evaporation of the solvent basification with sodium hydroxide was achieved. The base was extracted with ethyl acetate and the organic phase was washed, dried and evaporated to yield 21,5 g (90,7%) of crude 1-[3,3-bis(4-fluorophenyl)propyl]piperazine.

Workup

  1. filtrationThe catalyst was filtered off
  2. customafter evaporation of the solvent basification with sodium hydroxide
  3. extractionThe base was extracted with ethyl acetate
  4. washthe organic phase was washed
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-e3b635e191014f5f80c5db21e28d3dfb
Source dataset
uspto-grants-1993_08
Patent number
US05238939

Reaction notes

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