HCID 23285064, compound → HCID 23285016, compound

HRID 369192Notes

Reaction equation

HRID 369192 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:14]([N:16]2[CH2:21][CH2:20][CH:19]([N:22]([CH3:31])[CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:18][CH2:17]2)=[O:15])=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH:7]2SC>[Ni].CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:14]([N:16]2[CH2:17][CH2:18][CH:19]([N:22]([CH3:31])[CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:20][CH2:21]2)=[O:15])=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2

Participants

4

Reactant 1

HCID 23285064HCID 23285064, compound

Product 1

HCID 23285016HCID 23285016, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1.50 g of 7-chloro-3-methylthio-4-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-oxindole was added to a suspension of 15 g of Raney nickel in 30 ml of methanol. The mixture was stirred at room temperature for 1 hour. The Raney nickel was separated by decantation and washed with methanol. The decanted solution and the washings were combined and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (eluant: methylene chloride/methanol=30/1). The product was converted into a hydrochloride in ethanol to obtain 0.63 g of 7-chloro-4-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}oxindole hydrochloride as a colorless amorphous.

Workup

  1. customThe Raney nickel was separated by decantation
  2. washwashed with methanol
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by a silica gel column chromatography (eluant: methylene chloride/methanol=30/1)

Sources & evidence

ORD record
ord-c599f5a08e894917920fd56287bf1f28
Source dataset
uspto-grants-2000_10
Patent number
US06136826

Reaction notes

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