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

HRID 911267Notes

Reaction equation

HRID 911267 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-46ebcf5f274a4f37bcbc6c4dace87aac
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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