Piperidine → HCID 69883696, compound

HRID 2120195

Reaction equation

HRID 2120195 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)[CH:2]=1.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][C:20]=1[C:27]1[S:28][CH:29]=[CH:30][CH:31]=1.N1CCCCC1>C(O)C.CCOCC>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[C:11]2[C:10]3[C:14](=[CH:15][C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[CH:8][CH:9]=3)[NH:13][C:12]2=[O:16])=[CH:21][C:20]=1[C:27]1[S:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 219155796-Pyridin-3-yl-1,3-dihydro-indol-2-oneHCID 219810244-Methoxy-3-(thiophen-2-yl)benzaldehyde

Product 1

HCID 69883696HCID 69883696, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 6-pyridin-3-yl-1,3-dihydro-indol-2-one (100 mg, 0.5 mmol), 4-methoxy-3-thiophen-2-yl-benzaldehyde (110 mg, 0.5 mmol) and piperidine (0.23 mL) in ethanol (4 mL) was heated to reflux and stirred overnight. The reaction mixture was then cooled and diluted with ether to afford a precipitate which removed by filtration. Thefiltrate was column chromatographed (eluant—isopropanol/dichloromethane) to give 30 mg (15%) of 3-(4-methoxy-3-thiophen-2-yl-benzylidene)-6-pyridin-3-yl-1,3-dihydroindol-2-one as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was then cooled
  4. customto afford a precipitate which
  5. customremoved by filtration
  6. customThefiltrate was column chromatographed (eluant—isopropanol/dichloromethane)

Sources & evidence

ORD record
ord-109e72eee4dd4152a9a69a299f59271f
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Linked notes

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