Diethyl Ether → HCID 21446145, compound

HRID 597734Notes

Reaction equation

HRID 597734 reaction equation
[NH:1]1[C:6](=O)[CH2:5][CH2:4][C:3]2([CH2:12][CH:11]3[CH2:13][CH2:14][CH:8]2[CH2:9][CH2:10]3)[C:2]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[OH-].[Na+]>O>[NH:1]1[CH2:6][CH2:5][CH2:4][C:3]2([CH2:12][CH:11]3[CH2:13][CH2:14][CH:8]2[CH2:9][CH2:10]3)[CH2:2]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21446143Spiro[bicyclo[2.2.2]octane-2,3′-piperidine]-2′,6′-dione

Product 1

HCID 21446145HCID 21446145, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An amount of 50 g (0.24 mole) of spiro[bicyclo[2.2.2]octane-2,3'-piperidine]-2',6'-dione is introduced portionwise by means of a connecting tube in the course of 15-20 minutes, with stirring, into a mixture of 14 g (0.37 mole) of lithium aluminum hydride in 3 liters of abs. ether. The temperature during the addition is not to exceed 25°. The mixture is refluxed under nitrogen for 32 hours. After subsequent cooling, successive additions are made dropwise of 14 ml of water, 28 ml of 2N sodium hydroxide solution and a further 28 ml of water. The mixture is then stirred for 1 hour; it is afterwards filtered under reduced pressure and the residue subsequently well washed with ether. The filtrate is dried over sodium sulphate and concentrated by evaporation. The residue is fractionated in high vacuum to obtain spiro[bicyclo[2.2.2]octane-2,3'-piperidine], B.P. 95°-130°/0.2 Torr. From this base there is obtained, with excess ethereal hydrogen chloride solution, spiro[bicyclo[2.2.2]octane-2,3'-piperidine]-hydrochloride, M.P. 207°-208.5° (from acetone/ether).

Workup

  1. additionThe temperature during the addition
  2. customto exceed 25°
  3. temperatureThe mixture is refluxed under nitrogen for 32 hours
  4. filtrationit is afterwards filtered under reduced pressure
  5. washthe residue subsequently well washed with ether
  6. dry with materialThe filtrate is dried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-13ebeed7a14845afb994d185f53c9499
Source dataset
uspto-grants-1977_03
Patent number
US04015007

Reaction notes

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