1-Methylpiperazine → 5-[(4-Methyl-1-piperazinyl)-carbonyl]-6,7-dibromo-8-nitro-1,4-benzodioxane

HRID 1413173Notes

Reaction equation

HRID 1413173 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Br:8][C:9]1[C:18]([Br:19])=[C:17]([N+:20]([O-:22])=[O:21])[C:12]2[O:13][CH2:14][CH2:15][O:16][C:11]=2[C:10]=1[C:23](Cl)=[O:24]>>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:23]([C:10]2[C:11]3[O:16][CH2:15][CH2:14][O:13][C:12]=3[C:17]([N+:20]([O-:22])=[O:21])=[C:18]([Br:19])[C:9]=2[Br:8])=[O:24])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 205447556,7-Dibromo-8-nitro-1,4-benzodioxane-5-carbonyl chloride

Product 1

HCID 205447425-[(4-Methyl-1-piperazinyl)-carbonyl]-6,7-dibromo-8-nitro-1,4-benzodioxaneYield 69.6%

Conditions

Temperature
10 °C

Procedure

400 ml of methylethylcetone and 11 g of methylpiperazine were introduced into a balloon flask provided with an agitator and a thermometer. The mixture was cooled to 10° C. and then 41 g of 6,7-dibromo-8-nitro-1,4-benzodioxane-5-carbonyl chloride were added in portions with the temperature being maintained below 20° C. After agitation of the mixture, the crystals were dried off, washed with methylethylcetone and dried and then dissolved in water and reprecipitated by addition of 50 ml of 20% ammonia. The crystals were dried off, washed with water and dried. 33 g of 5-[(4-methyl-1-piperazinyl)-carbonyl]-6,7-dibromo-8-nitro-1,4-benzodioxane were obtained (M.P.: 164° C.; yield: 69.6%).

Workup

  1. customprovided with an agitator
  2. temperaturebeing maintained below 20° C
  3. customAfter agitation of the mixture, the crystals were dried off
  4. washwashed with methylethylcetone
  5. customdried
  6. dissolutiondissolved in water
  7. customreprecipitated by addition of 50 ml of 20% ammonia
  8. customThe crystals were dried off
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-d1188195df1940a18aa00ecc3859bab3
Source dataset
uspto-grants-1981_02
Patent number
US04248885

Reaction notes

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