Water → 2,5-Dibenzyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione

HRID 268225Notes

Reaction equation

HRID 268225 reaction equation
[CH:1]12[CH2:9][CH2:8][CH:4]([NH:5][C:6]1=[O:7])[C:3](=[O:10])[NH:2]2.[H-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C)C=O.C(OCC)C>[CH2:13]([N:2]1[C:3](=[O:10])[CH:4]2[CH2:8][CH2:9][CH:1]1[C:6](=[O:7])[N:5]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 128535912,5-Diazabicyclo[2.2.2]octane-3,6-dione

Product 1

HCID 215454902,5-Dibenzyl-2,5-diazabicyclo[2.2.2]octane-3,6-dioneYield 91.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A hot solution of 36.6 g (0.262 mole) of 2,5-diazabicyclo[2.2.2]octane-3,6-dione in 800 ml dry dimethylformamide was added rapidly from a dropping funnel to 12.5 g (0.52 mole) of oil-free sodium hydride. After stirring for 1 hour, the mixture was chilled and treated with 67.5 ml (0.59 mole) benzyl chloride during a period of a few minutes. After stirring at room temperature for 18 hours, 1 liter of water was added cautiously, and the mixture was extracted with chloroform. The extracts were washed with water, dried with sodium sulfate, and evaporated to dryness to yield a crystalline residue. Trituration in diethyl ether provided 77.0 g (91%) of product as colorless needles, melting point 168°-170°C.

Workup

  1. temperaturethe mixture was chilled
  2. stirringAfter stirring at room temperature for 18 hours
  3. extractionthe mixture was extracted with chloroform
  4. washThe extracts were washed with water
  5. dry with materialdried with sodium sulfate
  6. customevaporated to dryness
  7. customto yield a crystalline residue

Sources & evidence

ORD record
ord-e77d279ced6846dbb345781a5af7aebf
Source dataset
uspto-grants-1976_03
Patent number
US03947445

Reaction notes

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