Sodium Hydroxide → HCID 12665520, compound

HRID 2049326Notes

Reaction equation

HRID 2049326 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH:9]=2)[C:3]1=[O:15].[Br-].[Li+].[OH-].[Na+]>C(#N)C.CCCCCC>[OH:14][C:10]1[CH:9]=[C:8]([CH:4]2[CH2:5][CH2:6][CH2:7][N:2]([CH3:1])[C:3]2=[O:15])[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 82050Lithium BromideHCID 12665515HCID 12665515, compound

Product 1

HCID 12665520HCID 12665520, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

1-Methyl-3-(3-oxocyclohexen-1-yl)-2-piperidone (3.5 g) was refluxed in acetonitrile (100 ml) in the presence of lithium bromide (1.4 g) and cupric bromide (7.6 g) for 0.5 hours. The acetonitrile was evaporated to give a gum, to which 2 N sodium hydroxide (100 ml) was added, the solution filtered, conc. HCl (30 ml) added to the filtrate, the aqueous extracted with chloroform, dried (MgSO4) and evaporated to give an oil, which on standing overnight, at 0° C., in hexane gave a yellow solid. This was collected, washed with ether then acetone to give the title compound as the quarter hydrate, a colourless solid (0.50 g) m.p. 111°-114° C.

Workup

  1. customThe acetonitrile was evaporated
  2. customto give a gum
  3. filtrationthe solution filtered
  4. additionconc. HCl (30 ml) added to the filtrate
  5. extractionthe aqueous extracted with chloroform
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give an oil, which
  9. customgave a yellow solid
  10. customThis was collected
  11. washwashed with ether

Sources & evidence

ORD record
ord-6a3ad979de2b462790c8caa933eabc72
Source dataset
uspto-grants-1980_04
Patent number
US04197241

Reaction notes

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