2-Vinylpyridine → HCID 18993324, compound

HRID 375569Notes

Reaction equation

HRID 375569 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:14])[CH:8]2[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)=[CH2:22]>C(O)CCC.O.C(OCC)(=O)C>[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:14])[CH:8]2[CH2:13][CH2:12][CH2:11][N:10]([CH2:22][CH2:21][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 75212-VinylpyridineHCID 18993323HCID 18993323, compound

Product 1

HCID 18993324HCID 18993324, compoundYield 21.5%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(diphenylhydroxymethyl)piperidine (267 mg, 1.0 mmol), 2-vinylpyridine (0.32 g, 3.0 mol) and Triton B (3 drops) in 1-butanol (10 ml) was heated under reflux for 18 hours, diluted with water and ethyl acetate and the layers separated. The organic layer was washed with water, dried over magnesium sulphate and evaporated. The residue was twice taken up in toluene and evaporated and it was then purified by chromatography on SiO2 using dichloromethane plus 0-5% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (80 mg) as a pale brown oil which was characterised containing 0.25 equivalents of water.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customthe layers separated
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customevaporated
  8. customit was then purified by chromatography on SiO2
  9. customevaporated

Sources & evidence

ORD record
ord-cab29c9f35704bd7b87ebe607fe65c38
Source dataset
uspto-grants-1996_01
Patent number
US05486527

Reaction notes

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