Piperidine → HCID 69843383, compound

HRID 1604349Notes

Reaction equation

HRID 1604349 reaction equation
[CH2:1]([O:3][C:4](=[O:9])/[CH:5]=[CH:6]/[CH2:7]Br)[CH3:2].[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:9])/[CH:5]=[CH:6]/[CH2:7][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 5373944Ethyl (E)-4-bromobut-2-enoate

Product 1

HCID 69843383HCID 69843383, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl-4-bromocrotonate (193 mg), piperidine (94 mg) and potassium carbonate (276 mg) in acetonitrile (10 ml) was stirred and heated at reflux for 3 hours. The reaction mixture was cooled and the solvent was removed in vacuo. The residue was partitioned between water (2×15 ml) and ethyl acetate (20 ml). The organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as an orange oil (157 mg).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was removed in vacuo
  5. customThe residue was partitioned between water (2×15 ml) and ethyl acetate (20 ml)
  6. dry with materialThe organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc0b6c57f09c475f9484597acc5a6187
Source dataset
uspto-grants-1999_11
Patent number
US05994344

Reaction notes

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