4-Vinylpyridine → 1-{1-[2-(4-Pyridyl)ethyl]piperidin-4-yl}indoline

HRID 1790418Notes

Reaction equation

HRID 1790418 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[CH:16]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)=[CH2:17]>C(O)C>[N:21]1[CH:22]=[CH:23][C:18]([CH2:16][CH2:17][N:1]2[CH2:6][CH2:5][CH:4]([N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH2:9][CH2:8]3)[CH2:3][CH2:2]2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 75024-VinylpyridineHCID 220286031-Piperidin-4-yl-2,3-dihydro-1H-indole

Product 1

HCID 220380791-{1-[2-(4-Pyridyl)ethyl]piperidin-4-yl}indolineYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-Piperidyl)indoline (0.1 g) was dissolved in ethanol (5 ml). After adding 4-vinylpyridine (0.16 ml), the resultant mixture was heated under reflux in a nitrogen atmosphere for 12 hr. Then the reaction solution was concentrated under reduced pressure and purified by silica gel column chromatography (toluene/acetone system) to give the title compound (0.064 g) as a colorless oil (yield: 42.5%).

Workup

  1. temperatureunder reflux in a nitrogen atmosphere for 12 hr
  2. concentrationThen the reaction solution was concentrated under reduced pressure
  3. custompurified by silica gel column chromatography (toluene/acetone system)

Sources & evidence

ORD record
ord-2bb1e17f0a3f4e93b14ba3e801491e35
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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