Piperidine → HCID 25233387, compound

HRID 404672Notes

Reaction equation

HRID 404672 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C(#N)C>[N:14]1([CH:2]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[C:3]([O:5][CH3:6])=[O:4])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 10490396HCID 10490396, compound

Product 1

HCID 25233387HCID 25233387, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 2-bromo-2-p-tolylacetate (2.50 g, 10.3 mmol) in acetonitrile, was added piperidine (2.06 ml, 20.6 mmol) and the mixture was reacted for 2 hours at room temperature. The solvent was evaporated and the resulting crude was portioned between water and EtOAc. The aqueous phase was extracted with EtOAc, the organic phases were combined, dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by flash chromatography (petroleum ether/EtOAc=9/1) to obtain methyl 2-(piperidin-1-yl)-2-p-tolylacetate (273 mg, 21% yield) as a colourless oil.

Workup

  1. customthe mixture was reacted for 2 hours at room temperature
  2. customThe solvent was evaporated
  3. extractionThe aqueous phase was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude was purified by flash chromatography (petroleum ether/EtOAc=9/1)

Sources & evidence

ORD record
ord-fb99bab0d9da4a2c8aa8f2ac91768ebe
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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