Malononitrile → 1,4-Diazabicyclo[2.2.2]octane, hydrochloride

HRID 2271247Notes

Reaction equation

HRID 2271247 reaction equation
C(#N)CC#N.[CH2:6]1[N:11]2[CH2:12][CH2:13][N:8]([CH2:9][CH2:10]2)[CH2:7]1.[Cl-:14].[Li+]>O1CCCC1>[CH2:6]1[N:11]2[CH2:12][CH2:13][N:8]([CH2:9][CH2:10]2)[CH2:7]1.[ClH:14]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 9237DabcoHCID 433294Lithium Chloride

Product 1

HCID 5198321,4-Diazabicyclo[2.2.2]octane, hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 100 ml of anhydrous tetrahydrofurane under argon at 0° C., 20.27 g (100 mmoles) of 4-styrenesulfonyl chloride CH2═CHC6H4SO2Cl (commercially available from Monomer-Polymer & Dajac Laboratories), 10.42 g (100 mmoles) of malononitrile and 22.44 g (200 mmoles) of DABCO were reacted. After 2 hours at 0° C. and 48 hours at room temperature, the solution was filtered to remove the DABCO hydrochloride formed, and it was treated with 4.24 g of anhydrous lithium chloride (100 mmoles), stored and weighed in a glove box. There is immediately formed a precipitate of DABCO hydrochloride and the reaction mixture was then again filtered after stirring for 6 hours. After evaporation and drying under vacuum during 24 hours at room temperature, 31.16 g of the lithium salt of 4-styrenesulfonylmalononitrile were recovered, with a purity characterized by a proton and carbon RMN higher than 97%.

Workup

  1. filtration48 hours at room temperature, the solution was filtered
  2. customto remove the DABCO hydrochloride
  3. customformed
  4. customweighed in a glove box

Sources & evidence

ORD record
ord-ef591b1d936c46fe84260ef317fd7421
Source dataset
uspto-grants-2001_12
Patent number
US06333425B1

Reaction notes

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