HCID 86743986, compound → HCID 14423724, compound

HRID 2106649Notes

Reaction equation

HRID 2106649 reaction equation
O[N:2]=[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=3)[CH2:21][CH2:20]2)=[CH:11][CH:10]=1)[CH2:4][CH2:5][C:6](O)=[O:7].[H][H]>[Ni].CO>[CH3:31][C:27]1[CH:26]=[C:25]([N:22]2[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][CH2:15][C:12]3[CH:11]=[CH:10][C:9]([CH:3]4[NH:2][C:6](=[O:7])[CH2:5][CH2:4]4)=[CH:14][CH:13]=3)[CH2:24][CH2:23]2)[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 86743986HCID 86743986, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14423724HCID 14423724, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To 9.7 g of 4-hydroxyimino-4-[4-(4-(4-(3-methylphenyl)piperazin-1-yl)butyl)phenyl]butyric acid and 5 g of Raney nickel, 300 ml of methanol is added, and stirred for 9 hours in 70 atm hydrogen gas at 120° C. in an autoclave. After the completion of the reaction, the catalyst is removed by filtration, and the solvent is distilled off under reduced pressure. The resulting oily substance is purified by silica gel column chromatography and recrystallized from ethyl acetate to give 6.4 g of 5-[4-(4-(4-(3-methylphenyl)piperazin-1-yl)butyl)phenyl]pyrrolidin-2-one having a melting point of 114° to 116° C.

Workup

  1. customAfter the completion of the reaction
  2. customthe catalyst is removed by filtration
  3. distillationthe solvent is distilled off under reduced pressure
  4. customThe resulting oily substance is purified by silica gel column chromatography
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ff2d208d65204a52867ef0ceccf25714
Source dataset
uspto-grants-1990_06
Patent number
US04931443

Reaction notes

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