Triethylamine → HCID 23285054, compound

HRID 369193Notes

Reaction equation

HRID 369193 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:19]([N:21]2[CH2:26][CH2:25][CH:24]([N:27]([CH3:36])[CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:23][CH2:22]2)=[O:20])=[C:13]2[C:17]=1[NH:16][C:15](=[O:18])[CH2:14]2>C(O)C.[C].[Pd]>[ClH:8].[CH3:36][N:27]([CH:24]1[CH2:23][CH2:22][N:21]([C:19]([C:12]2[CH:11]=[CH:10][CH:9]=[C:17]3[C:13]=2[CH2:14][C:15](=[O:18])[NH:16]3)=[O:20])[CH2:26][CH2:25]1)[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 23285017HCID 23285017, compound

Product 1

HCID 23285054HCID 23285054, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

0.88 ml of triethylamine, 0.1 g of 10% palladium carbon were added to 20 ml of a solution of 0.86 g of 7-chloro-4-{4-[N-methyl-N-(2-phenylethyl)amino)-1-piperidinylcarbonyl}oxindole in ethanol. The mixture was subjected to hydrogenation at normal pressure at room temperature for 6 hours. The catalyst was removed by filtration. The filtrate was subjected to distillation to remove the solvent. The residue was dissolved in methylene chloride. The solution was water-washed, dried with anhydrous magnesium sulfate, 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 0.19 g of 4-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}oxindole hydrochloride as a colorless amorphous.

Workup

  1. customThe catalyst was removed by filtration
  2. distillationThe filtrate was subjected to distillation
  3. customto remove the solvent
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by a silica gel column chromatography (eluant: methylene chloride/methanol=30/1)

Sources & evidence

ORD record
ord-a63eacfe1eb44d579d2412189f01549e
Source dataset
uspto-grants-2000_10
Patent number
US06136826

Reaction notes

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