Piperidine → HCID 50908794, compound

HRID 2191401Notes

Reaction equation

HRID 2191401 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][C:9]2[NH:13][C:14]([CH:17]=O)=[C:15]([CH3:16])[C:8]=2[C:7]1=[O:19])[CH3:2].[F:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27](=[O:32])[CH2:26]2.N1CCCCC1>C(O)C>[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][CH:9]2[NH:13][C:14](/[CH:17]=[C:26]3\[C:27](=[O:32])[NH:28][C:29]4[C:25]\3=[CH:24][C:23]([F:22])=[CH:31][CH:30]=4)=[C:15]([CH3:16])[CH:8]2[C:7]1=[O:19])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 592500815-(2-Diethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde

Product 1

HCID 50908794HCID 50908794, compoundYield 80.76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(2-Diethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 1j (0.271 g, 0.93 mmol) and 5-fluoro-1,3-dihydro-indol-2-one (0.127 g, 0.84 mmol) were dissolved in 1.4 ml of anhydrous ethanol under stirring at room temperature, the resulting mixture was stirred for 10 minutes in dark, and added with piperidine (0.15 ml, 1.49 mmol). The mixture was refluxed at 70° C. for about 1.5 hours in an oil bath under an argon atmosphere and lots of orange precipitates were formed. After thin lay chromatography showed the disappearance of starting materials, the ice-salt bath was removed, and the reaction mixture was naturally cooled to room temperature, filtered and dried to obtain the title compound (Z)-5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-3 a,5,6,7,8,8a-hexahydro-1H-pyrrolo[3,2-c]azepin-4-one 1 (0.288 g, yield 80.76%) as an orange solid.

Workup

  1. stirringthe resulting mixture was stirred for 10 minutes in dark, and
  2. temperatureThe mixture was refluxed at 70° C. for about 1.5 hours in an oil bath under an argon atmosphere
  3. customlots of orange precipitates
  4. customwere formed
  5. customthe ice-salt bath was removed
  6. temperaturethe reaction mixture was naturally cooled to room temperature
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-449019d3d6e14e7d8c6dbf6374839e4f
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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