Ethylenediamine → HCID 15713145, compound

HRID 982300Notes

Reaction equation

HRID 982300 reaction equation
[CH3:1][CH:2]([CH2:7][CH2:8][C:9](=O)[CH3:10])[C:3]([O:5]C)=O.[CH2:12]([NH2:15])[CH2:13][NH2:14]>CCCCCCC>[CH3:10][CH:9]1[CH:8]2[N:15]([C:3](=[O:5])[CH:2]([CH3:1])[CH2:7]2)[CH2:12][CH2:13][NH:14]1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 13092228HCID 13092228, compound

Product 1

HCID 15713145HCID 15713145, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
38 °C

Procedure

124.2 g (0.75 mole) of methyl 2-methyl-5-oxohexanoate in 450 ml of n-heptane are initially taken. 52.2 g (0.87 mole) of ethylenediamine are then added dropwise at room temperature in the course of 10 minutes. As a result of the exothermic reaction, the temperature increases to 38° C. 49 ml of the lower phase (aqueous methanol) are separated off. The mixture is cooled to 2° C. and stirred for 1 hour, and the product is filtered off under suction, washed with cold n-heptane and dried. 116.3 g of racemic 5,8-dimethyl-9-oxo-1,4-diazabicyclo[4.3.0]nonane are obtained.

Workup

  1. customAs a result of the exothermic reaction
  2. custom49 ml of the lower phase (aqueous methanol) are separated off
  3. temperatureThe mixture is cooled to 2° C.
  4. filtrationthe product is filtered off under suction
  5. washwashed with cold n-heptane
  6. customdried

Sources & evidence

ORD record
ord-4d92cee3fe9e4739ac3a5ade0f7e7780
Source dataset
uspto-grants-1991_02
Patent number
US04995899

Reaction notes

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