HCID 20563093, compound → HCID 53694893, compound

HRID 1155202Notes

Reaction equation

HRID 1155202 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]([CH:21]1[CH:26]([OH:27])[CH2:25][CH2:24][CH2:23][N:22]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CC(C)=O>[CH2:14]([CH:21]1[C:26](=[O:27])[CH2:25][CH2:24][CH2:23][N:22]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 20563093HCID 20563093, compoundHCID 131709961Jones' reagent

Product 1

HCID 53694893HCID 53694893, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones' reagent (116.1 ml) was added dropwise to a stirred solution of 2-n-heptyl-3-hydroxy-1-n-octyl-piperidine (16.6 g) in acetone (160 ml) at room temperature. The reaction mixture was stirred for 6 hours and filtered through kieselguhr. The residue was washed several times with ether and the combined organic solutions were extracted with 5% sodium hydroxide solution. The aqueous phase was washed with ether and the combined organic phases were washed with water, dried over magnesium sulphate and evaporated in vacuo. The product was purified by chromatography to give 2-n-heptyl-1-n-octyl-piperidin-3-one as a yellow gum (5.71 g, 34% yield).

Workup

  1. filtrationfiltered through kieselguhr
  2. washThe residue was washed several times with ether
  3. extractionthe combined organic solutions were extracted with 5% sodium hydroxide solution
  4. washThe aqueous phase was washed with ether
  5. washthe combined organic phases were washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated in vacuo
  8. customThe product was purified by chromatography

Sources & evidence

ORD record
ord-1aa591e73450495892c47780316f82b1
Source dataset
uspto-grants-1981_11
Patent number
US04299970

Reaction notes

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