3-Cyclobutene-1,2-dione, 3,4-dimethoxy- → HCID 21423011, compound

HRID 259076Notes

Reaction equation

HRID 259076 reaction equation
[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)[CH2:2][CH3:3].CO[C:13]1[C:14](=O)[C:15](=[O:19])[C:16]=1[O:17]C>CO>[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:13]2[C:16](=[O:17])[C:15](=[O:19])[C:14]=2[N:7]2[CH2:8][CH2:9][CH2:10][N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 122617971-propyl-1,4-diazepane

Product 1

HCID 21423011HCID 21423011, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3.1 grams of 1-propylhomopiperazine in 20 ml. of methanol is mixed with a solution of 1.6 grams of 3,4-dimethoxy-3-cyclobutene-1,2-dione in 50 ml. of methanol and refluxed under nitrogen for 5 hours. The methanol solvent is evaporated by heating on a steam bath and the residual solid is dissolved in 70 ml. of anhydrous benzene at room temperature, treated with charcoal, and filtered. The resulting filtrate is diluted with 250 ml. of hexane and the precipitate which forms is separated by filtration and dried and then recrystallized from 1000 ml. of refluxing hexane to give 3,4-bis(4-propyl-1-homopiperazinyl)-3-cyclobutene-1,2-dione as white crystals melting at about 90°-92° C.

Workup

  1. customThe methanol solvent is evaporated
  2. temperatureby heating on a steam bath
  3. dissolutionthe residual solid is dissolved in 70 ml
  4. additionof anhydrous benzene at room temperature, treated with charcoal
  5. filtrationfiltered
  6. additionThe resulting filtrate is diluted with 250 ml
  7. customof hexane and the precipitate which forms is separated by filtration
  8. customdried
  9. customrecrystallized from 1000 ml

Sources & evidence

ORD record
ord-e65694aedc844750a977ffe2dcb6d116
Source dataset
uspto-grants-1977_07
Patent number
US04036828

Reaction notes

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