Hydrochloric Acid → 1-Ethylcarbonyl-4-oxohomopiperidine

HRID 242536Notes

Reaction equation

HRID 242536 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl.[C:10]([O-:13])([O-])=O.[K+].[K+].ClC(O[CH2:20][CH3:21])=O>C1COCC1>[CH2:20]([C:10]([N:5]1[CH2:6][CH2:7][CH2:8][C:2](=[O:1])[CH2:3][CH2:4]1)=[O:13])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 1501891Azepan-4-one

Product 1

HCID 186757361-Ethylcarbonyl-4-oxohomopiperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) stirred solution of 4-oxohomopiperidine.HCl (0.6 g, 4.05 mmol), K2CO3 (0.615 g, 4.46 mmol) in anhydrous THF (10 mL) will be ethyl chloroformate (0.44 mL, 4.05 mmol) dropwise. The reaction was warmed to RT for 2 hrs then quenched with H2O, extracted with EtOAc, and the organic layer dried over Na2SO4. Pure 1-ethylcarbonyl-4-oxohomopiperidine will be isolated via silica gel flash chromatography

Workup

  1. customthen quenched with H2O
  2. extractionextracted with EtOAc
  3. dry with materialthe organic layer dried over Na2SO4

Sources & evidence

ORD record
ord-216e08c4c84c42deadf343597b24b5f1
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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