Gamma-Butyrolactone → 1,5-Diazabicyclo(4.3.0)non-5-ene

HRID 1276598Notes

Reaction equation

HRID 1276598 reaction equation
[C:1]1(=O)O[CH2:4][CH2:3][CH2:2]1.[CH2:7]([CH2:10][NH3+:11])[CH2:8][NH3+:9]>>[CH2:3]1[CH2:4][N:11]2[C:1](=[N:9][CH2:8][CH2:7][CH2:10]2)[CH2:2]1

Participants

3

Reactant 2

HCID 7302Gamma-ButyrolactoneHCID 4030255HCID 4030255, compound

Product 1

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneYield 47.2%

Procedure

Using a method similar to Example 1, 25.4 mol of butyrolactone were reacted with 35 mol of 1,3-DAP (molar ratio=1.38). After a reaction time of 32 hours, the temperature of the liquid in the flask was 220° C. and 73% of the theoretically possible amount of water had been distilled off. Distillation gave 12 mol of DBN having a purity of more than 99.1%. The total yield of DBN, including the amount still present in the distillation residues, was 83.3%.

Workup

  1. customAfter a reaction time of 32 hours
  2. customwas 220° C.
  3. distillation73% of the theoretically possible amount of water had been distilled off
  4. distillationDistillation

Sources & evidence

ORD record
ord-96879271b73442a0bbe1358b16766135
Source dataset
uspto-grants-2000_12
Patent number
US06166207

Reaction notes

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