Hydrochloric Acid → 1-Ethylcarbonyl-4-oxohomopiperidine

HRID 457047Notes

Reaction equation

HRID 457047 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-651e4369b41c4937b002b3e1aa26a4e2
Source dataset
uspto-grants-2007_03
Patent number
US07186729B2

Reaction notes

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