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

HRID 44279Notes

Reaction equation

HRID 44279 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-a1da0f631a624ed1a0bc9bbd03927ae9
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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