Sodium hydride → HCID 14178413, compound

HRID 2235229Notes

Reaction equation

HRID 2235229 reaction equation
[CH:1]1([NH:7][C:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+]>C1COCC1>[CH:1]1([N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 116729745-Chloro-N-cyclohexylpentanamide

Product 1

HCID 14178413HCID 14178413, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Take up the 5-chloro-pentanoic acid cyclohexylamide in THF (700 mL), add sodium hydride (31 g, 60% dispersion on mineral oil, 775 mmol) and heat at 70° C. 19 h. Cool the mixture, filter through a fritted funnel, wash the filtrate with brine, dry the organic layer over sodium sulfate and evaporate. Purify the residue by column chromatography on silica gel (eluting 50% to 100% ethyl acetate) to obtain 1-cyclohexyl-piperidin-2-one as a beige solid (8.8 g, 63%). MS (EI) m/z=181 (M+).

Workup

  1. custom19 h
  2. temperatureCool the mixture
  3. filtrationfilter through a fritted funnel
  4. washwash the filtrate with brine
  5. dry with materialdry the organic layer over sodium sulfate
  6. customevaporate
  7. customPurify the residue by column chromatography on silica gel (eluting 50% to 100% ethyl acetate)

Sources & evidence

ORD record
ord-e05bdfc5b4bc4509a7791cfb1ad9da94
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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