Chloroacetyl chloride → 2-Chloro-1-piperidine-1-yl-ethanone

HRID 2041154Notes

Reaction equation

HRID 2041154 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].C(=O)([O-])[O-].[K+].[K+].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C1COCC1.O>[Cl:1][CH2:2][C:3]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:4]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8082PiperidineHCID 11430Potassium Carbonate

Product 1

HCID 2223122-Chloro-1-piperidine-1-yl-ethanoneYield 102.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add chloroacetyl chloride (1.242 g, 11.0 mmol) to a mixture of potassium carbonate (2.073 g, 15 mmol) and piperidine (852 mg, 10 mmol) in THF (50 mL) at 0° C. Stir the reaction for 12 h and gradually raise to room temperature. Dilute with water, extract with EtOAc three times. Combine the organic extracts and wash sequentially with saturated aqueous NaHCO3, 0.1N aqueous HCl and brine. Dry over Na2SO4, filter and concentrate to give the title compound (1.65 g, 100%).

Workup

  1. customthe reaction for 12 h
  2. extractionextract with EtOAc three times
  3. washCombine the organic extracts and wash sequentially with saturated aqueous NaHCO3, 0.1N aqueous HCl and brine
  4. dry with materialDry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-4cea2a41c1e943b682dc8dca3b542fc3
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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