Piperidine → 3-(3-Pyridyl)-1-(3-(tert-butoxycarbonylmethoxy)phenyl)-2-propen-1-one

HRID 426397Notes

Reaction equation

HRID 426397 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][C:10]1[CH:11]=[C:12]([C:16](=[O:18])[CH3:17])[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1.N1CCCCC1>CCO>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([CH:19]=[CH:17][C:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:11]=2)=[O:18])[CH:21]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 103713-Pyridinecarboxaldehyde2×HCID 22128939HCID 22128939, compound

Product 1

HCID 539427043-(3-Pyridyl)-1-(3-(tert-butoxycarbonylmethoxy)phenyl)-2-propen-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 16 (4.0 g, 16 mmol), nicotinaldehyde (1.89 mL, 20 mmol), and piperidine (4.0 mL, 40 mmol) in absolute EtOH (65 mL) was heated at reflux for 16 h. The mixture was cooled and concentrated in vacuo. Chromatography on silica gel (30-60% EtOAc/hexanes) gave a mixture of unreacted nicotinaldehyde and 17 (both have the same Rf on TLC). Washing of the mixture with hexane in a filter funnel provide 1.73 g (32%) of pure 17 as a yellow crystal. 1H NMR (CDCl3, 300 MHz) 8.87 (d, J=2.1 Hz, 1H), 8.66 (dd, J=4.8, 1.5 Hz, 1H), 7.97 (d, J=7.9 Hz, 1H), 7.80 (d, J=16.7 Hz, 1H), 7.66 (d, J=7.6 Hz, 1H), 7.60 (d, J=15.9 Hz, 1H), 7.55 (s, 1H), 7.46 (t, J=7.8 Hz, 1H), 7.38 (dd, J=7.9, 4.8 Hz, 1H), 7.20 (dd, J=8.2, 2.6 Hz, 1H), 4.62 (s, 2H), 1.52 (s, 9H); 13C NMR (CDCl3, 75 MHz) 189.7, 175.0, 168.0, 158.7, 151.6, 150.5, 141.4, 139.5, 134.9, 131.0, 130.2, 124.2, 122.3, 120.6, 114.1, 83.1, 66.2, 28.4.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customChromatography on silica gel (30-60% EtOAc/hexanes) gave
  6. washWashing of the mixture with hexane in a filter funnel

Sources & evidence

ORD record
ord-0256ff08df634f4a9d1a007429a8343d
Source dataset
uspto-grants-2012_01
Patent number
US08106191B2

Reaction notes

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