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1-(1-Methyl-4-piperidinyl)piperazine → 4-(1-Methyl-piperidin-4-yl)-piperazine-1-carboxylic acid [3-(2-ethoxy-phenyl)-5-methoxy-2-oxo-2,3-dihydro-1H-indol-3-yl]-amide

HRID 601778
Notes
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Reaction equation

HRID 601778 reaction equation
C1([O:7][C:8](=O)[NH:9][C:10]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH2:29][CH3:30])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[NH:12][C:11]2=[O:21])C=CC=CC=1.[CH3:32][N:33]1[CH2:38][CH2:37][CH:36]([N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:35][CH2:34]1>C1COCC1>[CH2:29]([O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:10]1([NH:9][C:8]([N:42]2[CH2:41][CH2:40][N:39]([CH:36]3[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]3)[CH2:44][CH2:43]2)=[O:7])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[NH:12][C:11]1=[O:21])[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 57517779[3-(2-Ethoxy-phenyl)-5-methoxy-2-oxo-2,3-dihydro-1H-indol-3-yl]-carbamic acid phenyl ester

Product 1

HCID 575177804-(1-Methyl-piperidin-4-yl)-piperazine-1-carboxylic acid [3-(2-ethoxy-phenyl)-5-methoxy-2-oxo-2,3-dihydro-1H-indol-3-yl]-amideYield 65.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.9 g (4.5 mmol) of the intermediate from step D and 1.75 g (9.5 mmol) 1-(1-methylpiperidine-4-yl)-piperazine were dissolved in 30 ml dry THF and refluxed for 90 minutes. The volatiles were removed in vacuo. The resulting residue was dissolved in ethyl acetate, washed with H2O and dried over magnesium sulfate and the solvent was removed in vacuo. The residue was treated with H2O and the resulting precipitate was separated to yield 1.5 g of the intermediate.

Workup

  1. temperaturerefluxed for 90 minutes
  2. customThe volatiles were removed in vacuo
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. washwashed with H2O
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. additionThe residue was treated with H2O
  8. customthe resulting precipitate was separated

Sources & evidence

ORD record
ord-3c94edebc12e4bf2865fdc8a0596b107
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902379B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes