Piperidine → 1-Piperidineacetic acid, ethyl ester

HRID 352195Notes

Reaction equation

HRID 352195 reaction equation
Br[CH2:2][CH2:3][O:4][C:5](=[O:7])[CH3:6].CCN(CC)CC.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>O1CCCC1>[CH2:3]([O:4][C:5](=[O:7])[CH2:6][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 135641-Acetoxy-2-bromoethane

Product 1

HCID 6434661-Piperidineacetic acid, ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of bromoethylacetate, 3.3 g (30.0 mmol) in 100 mL of tetrahydrofuran was added 4.2 mL (30.0 mmol) of Et3N and 9 mL (90.0 mmol) of piperidine. The reaction mixture stirred overnight at rt. and was concentrated to dryness. The residue was partitioned between chloroform and saturated aqueous NaHCO3. The mixture was washed with saturated NaHCO3, washed with brine, dried over Na2SO4, filtered and concentrated to dryness to give 4.6 g (89%) of the desired product as a tan oil.

Workup

  1. concentrationand was concentrated to dryness
  2. customThe residue was partitioned between chloroform and saturated aqueous NaHCO3
  3. washThe mixture was washed with saturated NaHCO3
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7989397a82ec49b1a43eb8297064ea67
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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