Acetone → 5-[(4-Methyl-1-piperazinyl)-carbonyl]-7-nitro-1,4-benzodioxane

HRID 1660009Notes

Reaction equation

HRID 1660009 reaction equation
O.[N+:2]([C:5]1[CH:6]=[C:7]([C:15]([OH:17])=O)[C:8]2[O:13][CH2:12][CH2:11][O:10][C:9]=2[CH:14]=1)([O-:4])=[O:3].CC(C)=O.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(N(CC)CC)C>[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:15]([C:7]2[C:8]3[O:13][CH2:12][CH2:11][O:10][C:9]=3[CH:14]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=2)=[O:17])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 531671-MethylpiperazineHCID 124645337-Nitro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid

Product 1

HCID 205447095-[(4-Methyl-1-piperazinyl)-carbonyl]-7-nitro-1,4-benzodioxaneYield 66.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
10 °C

Procedure

22 ml of water, 22.5 g of 7-nitro-1,4-benzodioxane-5-carboxylic acid, 65 ml of acetone and 10.5 g of triethylamine were introduced into a 250 ml balloon flask provided with an agitator and a thermometer. The mixture was cooled to 10° C. and then 14 g of isobutyl chloroformiate was added. The mixture was agitated and the temperature allowed to rise. The oily compound formed was cooled to 10° C., 11 g of N-methyl piperazine was added and then the mixture was agitated, allowing the temperature to rise. The crystals formed were washed with water. 20.5 g of 5-[(4-methyl-1-piperazinyl)-carbonyl]-7-nitro-1,4-benzodioxane was produced (M.P.: 218° C.; yield: 66.7%).

Workup

  1. customprovided with an agitator
  2. addition14 g of isobutyl chloroformiate was added
  3. customThe oily compound formed
  4. temperaturewas cooled to 10° C.
  5. stirringthe mixture was agitated
  6. customThe crystals formed
  7. washwere washed with water

Sources & evidence

ORD record
ord-e167032f91c34bef8947d7e90b2f88f2
Source dataset
uspto-grants-1981_12
Patent number
US04306072

Reaction notes

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