Piperidine → HCID 25233388, compound

HRID 404675Notes

Reaction equation

HRID 404675 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>C1COCC1>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH:2]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[C:3]([O:5][CH3:6])=[O:4])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 10753737Methyl 2-bromo-2-(4-methoxyphenyl)acetate

Product 1

HCID 25233388HCID 25233388, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-bromo-2-(4-methoxyphenyl)acetate (2.5 g, 9.65 mmol) in THF (50 ml), was added piperidine (1.64 g, 19.3 mmol) and the mixture 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=85/15) to obtain (methyl 2-(4-methoxyphenyl)-2-(piperidin-1-yl)acetate (1.81 g, 71.4% yield).

Workup

  1. customthe mixture 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=85/15)

Sources & evidence

ORD record
ord-463b25eb82b64fa2a7d85c93f62bf34c
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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