Piperidine → 3-(3,5-Dimethyl-1H-pyrrol-2-ylmethylene)-5-(2-oxo-oxazolidin-3-ylmethyl)-1,3-dihydro-indol-2-one

HRID 241733Notes

Reaction equation

HRID 241733 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11]3)[CH2:5][CH2:4][O:3]1.[CH3:18][C:19]1[CH:23]=[C:22]([CH3:24])[NH:21][C:20]=1[CH:25]=O.N1CCCCC1>C(O)C>[CH3:18][C:19]1[CH:23]=[C:22]([CH3:24])[NH:21][C:20]=1[CH:25]=[C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([CH2:7][N:6]3[CH2:5][CH2:4][O:3][C:2]3=[O:1])[CH:9]=2)[NH:13][C:12]1=[O:17]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2704653,5-Dimethyl-1H-pyrrole-2-carbaldehydeHCID 666361565-(2-Oxo-oxazolidin-3-ylmethyl)-1,3-dihydro-indol-2-one

Product 1

HCID 666363323-(3,5-Dimethyl-1H-pyrrol-2-ylmethylene)-5-(2-oxo-oxazolidin-3-ylmethyl)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(2-oxo-oxazolidin-3-ylmethyl)-1,3-dihydro-indol-2-one (4.3 mmoles), 3,5-dimethyl-1H-pyrrole-2-carbaldehyde (5.17 mmoles) and piperidine (3 mmoles) in ethanol (30 ml) is heated at reflux for 24 hours. The solid formed is filtered off, washed with ethanol, with water and then with ethanol and dried in vacuo to yield the title product.

Workup

  1. temperatureat reflux for 24 hours
  2. customThe solid formed
  3. filtrationis filtered off
  4. washwashed with ethanol, with water
  5. dry with materialwith ethanol and dried in vacuo

Sources & evidence

ORD record
ord-aec92611ce764018841a7c927e0ad948
Source dataset
uspto-grants-2014_02
Patent number
US08653073B2

Reaction notes

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