Piperidine → HCID 69843383, compound

HRID 324004Notes

Reaction equation

HRID 324004 reaction equation
Br/[C:2](=[CH:8]\[CH3:9])/[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:6]([O:5][C:3](=[O:4])/[CH:2]=[CH:8]/[CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH3:7]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 5466635HCID 5466635, compound

Product 1

HCID 69843383HCID 69843383, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl 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). Tlc Silica. (100:8:1)Mixture of dichloromethane, ethanol and ammonia (S.G=0.88) Rf=0.55 Mass spec MH+ (found)=198 MH+ (calculated)=198.

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-8c97c5b68c9a465d84f567e6d5e446cc
Source dataset
uspto-grants-2001_04
Patent number
US06215002B1

Reaction notes

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