Triethylamine → HCID 23285054, compound

HRID 962791Notes

Reaction equation

HRID 962791 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-79e8b98c0f4244e895c33b5822a7d28a
Source dataset
uspto-grants-1998_06
Patent number
US05760058

Reaction notes

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