Diethylene Glycol → HCID 21393430, compound

HRID 461338Notes

Reaction equation

HRID 461338 reaction equation
[CH3:1][N:2]1[CH2:21][CH2:20][N:5]2[C:6]3[CH:19]=[CH:18][N:17]=[CH:16][C:7]=3[C:8](=O)[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH:4]2[CH2:3]1.C(O)COCCO.[OH-].[K+].O.NN>CS(C)=O>[CH3:1][N:2]1[CH2:21][CH2:20][N:5]2[C:6]3[CH:19]=[CH:18][N:17]=[CH:16][C:7]=3[CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH:4]2[CH2:3]1

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 21393415HCID 21393415, compound

Product 1

HCID 21393430HCID 21393430, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

800 mg (0.00285 mol) 2-methyl-10-oxo-1,2,3,4,10,14b-hexahydro-benzo[c]pyrazino[1,2-a]pyrido[3,4-f]azepine is added to a well-stirred suspension consisting of 4 ml di-ethylene glycol, 1 ml DMSO, 0.4 g KOH and 1 ml 80% hydrazine hydrate. The reaction is exothermic; the temperature of the reaction mixture is adjusted to 120° C and held there for 30 minutes. During this period hydrazine/water (0.8 ml) is distilled off, and the reaction temperature is then raised to 160° C for 2 hours. The reaction mixture is subsequently cooled, poured into water, and extracted with ether. After drying, and removing the solvent by evaporation, 685 mg (90%) 2-methyl-1,2,3,4,10,14b-hexahydro-benzo[c]pyrazino[1,2-a]pyrido[3,4-f]azepine is obtained as a light yellow oil.

Workup

  1. customis adjusted to 120° C
  2. distillationDuring this period hydrazine/water (0.8 ml) is distilled off
  3. temperatureThe reaction mixture is subsequently cooled
  4. additionpoured into water
  5. extractionextracted with ether
  6. customAfter drying
  7. customremoving the solvent
  8. customby evaporation

Sources & evidence

ORD record
ord-d67ad62c8210498e81a6682e1ee6eed0
Source dataset
uspto-grants-1977_12
Patent number
US04062848

Reaction notes

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