HCID 11583787, compound → HCID 11306161, compound

HRID 2374285Notes

Reaction equation

HRID 2374285 reaction equation
[C:1]1([C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[O:17])[CH2:5][CH2:4][CH2:3][CH:2]=1>CO.[Pd]>[CH:1]1([C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:16]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:31])[F:33])=[CH:28][CH:29]=3)[CH2:22][CH2:23]2)=[O:17])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 11583787HCID 11583787, compound

Product 1

HCID 11306161HCID 11306161, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2-Cyclopent-1-enyl-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone (Example 74) is hydrogenated in MeOH in presence of 10% Pd/C under a hydrogen pressure of 50 bar at 50° C. for 18h. Filtration, evaporation of the solvent and purification of the residue by preparative HPLC on a C-18 column with a H2O/MeCN gradient provided (2-Cyclopentyl-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone in 94% yield as colourless foam (M+H+: 481.5.).

Workup

  1. customat 50° C.
  2. customfor 18h
  3. filtrationFiltration, evaporation of the solvent and purification of the residue by preparative HPLC on a C-18 column with a H2O/MeCN gradient

Sources & evidence

ORD record
ord-dab920330243462084de8f28ad29ad79
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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